Pyridine → N-(4-(1-acetylpyrrolidin-2-yl)-3-fluorophenyl)pyrazine-2-carboxamide

HRID 13412Notes

Reaction equation

HRID 13412 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].N1C=CC=CC=1.Cl.Cl.[F:16][C:17]1[CH:18]=[C:19]([NH:28][C:29]([C:31]2[CH:36]=[N:35][CH:34]=[CH:33][N:32]=2)=[O:30])[CH:20]=[CH:21][C:22]=1[CH:23]1[CH2:27][CH2:26][CH2:25][NH:24]1>C(Cl)(Cl)Cl>[C:1]([N:24]1[CH2:25][CH2:26][CH2:27][CH:23]1[C:22]1[CH:21]=[CH:20][C:19]([NH:28][C:29]([C:31]2[CH:36]=[N:35][CH:34]=[CH:33][N:32]=2)=[O:30])=[CH:18][C:17]=1[F:16])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 23145221N-(3-fluoro-4-pyrrolidin-2-ylphenyl)pyrazine-2-carboxamide dihydrochloride

Product 1

HCID 23145506N-(4-(1-acetylpyrrolidin-2-yl)-3-fluorophenyl)pyrazine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.5 ml of acetic anhydride was added to a pyridine (50 ml) solution of 4.3 g of N-(3-fluoro-4-pyrrolidin-2-ylphenyl)pyrazine-2-carboxamide dihydrochloride, and the reaction liquid was stirred at room temperature for 20 minutes. The reaction liquid was diluted with chloroform, washed with water and saturated saline in order, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=50/1) to obtain the entitled compound as a yellow solid.

Workup

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. washwashed with water and saturated saline in order
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-732a7fe3fba64e73aa28b2f44c4de292
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

Loading…