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Novel Process For The Preparation Of 4 [N (5,6 Diphenylpyrazin 2 Yl) N Isopropylamino] 1 Butanol

Abstract: Provided herein is a novel, commercially viable and industrially advantageous process for the preparation of 4-pST-(5,6-diphenylpyrazm-2-yl)-N-isopropylamino]-1 -butanol.

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Patent Information

Application #
Filing Date
11 March 2020
Publication Number
38/2021
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
shinyadv@gmail.com
Parent Application

Applicants

SYMED LABS LIMITED
#8-2-293/174/3, Beside BN Reddy Colony, Road No.14, Banjara Hills, Hyderabad, Telangana, India, Pin code 500 034.

Inventors

1. SPANDANA TELUKUNTA
15-21-150/op/6/1, New Balaji Nagar, Near Saibaba temple, Kukatpally Hyderabad

Specification

We Claim:
1. A process for the preparation of 4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]-l-butanol of formula I:
which comprises:
reacting 2-chloro-5,6-diphenylpyrazine of formula III:
with 4-(isopropylamino)-l-butanol of formula II:
in the presence of an alkali metal bromide, or in the presence of potassium iodide, to produce the compound of formula I or a salt thereof, and optionally purifying and/or recrystallizing the resulting compound of formula I or a salt thereof with a suitable solvent or a mixture of suitable solvents to produce highly pure compound of formula I.
The process as claimed in claim 1, wherein the alkali metal bromide used in the reaction is selected from the group consisting of lithium bromide, sodium bromide and potassium bromide.

3. The process as claimed in claim 2, wherein the alkali metal bromide used in the reaction is potassium bromide.
4. The process as claimed in claim 1, wherein the compound, 4-(isopropylamino)-1-butanol, of formula II is used in the reaction in a ratio of less than about 4 molar equivalents with respect to the quantity 2-chloro-5,6-diphenylpyrazine of formula III in order to ensure a proper course of the reaction; wherein the potassium bromide is used in the reaction in a ratio of less than about 1 molar equivalents with respect to the quantity 2-chloro-5,6-diphenylpyrazine of formula III in order to ensure a proper course of the reaction; and/or wherein the potassium iodide is used in the reaction in a ratio of less than about 0.1 molar equivalents with respect to the quantity 2-chloro-5,6-diphenylpyrazine of formula III in order to ensure a proper course of the reaction.
5. The process as claimed in claim 4, wherein the compound, 4-(isopropylamino)-1-butanol, of formula II is used in the reaction in a ratio of 3.3 molar equivalents with respect to the quantity 2-chloro-5,6-diphenylpyrazine of formula III; wherein the potassium bromide is used in the reaction in a ratio of less than about 0.5 molar equivalents with respect to the quantity 2-chloro-5,6-diphenylpyrazine of formula III; and/or wherein the potassium iodide is used in the reaction in a ratio of less than about 0.05 molar equivalents with respect to the quantity 2-chloro-5,6-diphenylpyrazine of formula III.
6. The process as claimed in claim 1, wherein the reaction is carried out at a temperature of about 20°C to about 200°C; wherein the compound of formula I or a salt thereof is isolated and/or re-crystallized from a suitable solvent by conventional methods such as cooling, seeding, partial removal of the solvent from the solution, by adding an anti-solvent to the solution, evaporation, vacuum distillation, or a combination thereof; and wherein the solvent used for isolating, purifying and/or recrystallizing the compound of formula I is selected from the group consisting of water, an alcohol, a ketone, an ether, an ester, a hydrocarbon, a halogenated hydrocarbon, and mixtures thereof.

7. The process as claimed in claim 6, wherein the reaction is carried out at a temperature of about 100°C to about 180°C; and wherein the solvent used for isolating, purifying and/or recrystallizing the compound of formula I is selected from the group consisting of water, methanol, ethanol, 1-propanol, isopropyl alcohol, acetone, diisopropyl ether, methyl tert-butyl ether, n-hexane, ethyl acetate, butyl acetate, cyclohexane, toluene, xylene, dichloromethane, dichloroethane, chloroform, and mixtures thereof.
8. The process as claimed in claim 1, wherein the compound 4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropy!amino]-l-butanol of formula I or a salt thereof obtained has a purity of greater than about 90% as measured by HPLC,
9. The process as claimed in claim 8, wherein the compound 4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]-l-butanol of formula I or a salt thereof obtained has a purity of greater than about 95% as measured by HPLC.
10. The process as claimed in claim 8, wherein the compound 4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]-l-butanol of formula I or a salt thereof obtained has a purity of greater than about 98% as measured by HPLC.

Documents

Application Documents

# Name Date
1 202041010268-FORM 18 [29-02-2024(online)].pdf 2024-02-29
1 202041010268-STATEMENT OF UNDERTAKING (FORM 3) [11-03-2020(online)].pdf 2020-03-11
2 202041010268-FORM 1 [11-03-2020(online)].pdf 2020-03-11
2 202041010268-Correspondence_Power of Attorney, Assignment_30-03-2021.pdf 2021-03-30
3 202041010268-COMPLETE SPECIFICATION [11-03-2020(online)].pdf 2020-03-11
3 202041010268-8(i)-Substitution-Change Of Applicant - Form 6 [09-03-2021(online)].pdf 2021-03-09
4 202041010268-Annexure [09-03-2021(online)].pdf 2021-03-09
4 202041010268-Correspondence_Form3_27-08-2020.pdf 2020-08-27
5 202041010268-FORM-26 [04-09-2020(online)].pdf 2020-09-04
5 202041010268-ASSIGNMENT DOCUMENTS [09-03-2021(online)].pdf 2021-03-09
6 202041010268-PA [09-03-2021(online)].pdf 2021-03-09
6 202041010268-ENDORSEMENT BY INVENTORS [04-09-2020(online)].pdf 2020-09-04
7 202041010268-Correspondence_Form2-Form5 and Form26_07-09-2020.pdf 2020-09-07
8 202041010268-PA [09-03-2021(online)].pdf 2021-03-09
8 202041010268-ENDORSEMENT BY INVENTORS [04-09-2020(online)].pdf 2020-09-04
9 202041010268-FORM-26 [04-09-2020(online)].pdf 2020-09-04
9 202041010268-ASSIGNMENT DOCUMENTS [09-03-2021(online)].pdf 2021-03-09
10 202041010268-Annexure [09-03-2021(online)].pdf 2021-03-09
10 202041010268-Correspondence_Form3_27-08-2020.pdf 2020-08-27
11 202041010268-8(i)-Substitution-Change Of Applicant - Form 6 [09-03-2021(online)].pdf 2021-03-09
11 202041010268-COMPLETE SPECIFICATION [11-03-2020(online)].pdf 2020-03-11
12 202041010268-FORM 1 [11-03-2020(online)].pdf 2020-03-11
12 202041010268-Correspondence_Power of Attorney, Assignment_30-03-2021.pdf 2021-03-30
13 202041010268-STATEMENT OF UNDERTAKING (FORM 3) [11-03-2020(online)].pdf 2020-03-11
13 202041010268-FORM 18 [29-02-2024(online)].pdf 2024-02-29
14 202041010268-FER.pdf 2025-10-16

Search Strategy

1 202041010268_SearchStrategyNew_E_SearchHistoryE_16-10-2025.pdf