Methyl 3-aminopyrazinecarboxylate → HCID 57942622, compound

HRID 1898009Notes

Reaction equation

HRID 1898009 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][C:14]=1[C:23]([F:26])([F:25])[F:24]>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][S:19]([C:16]2[CH:17]=[CH:18][C:13]([Cl:12])=[C:14]([C:23]([F:26])([F:24])[F:25])[CH:15]=2)(=[O:21])=[O:20])=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 72669Methyl 3-aminopyrazinecarboxylateHCID 27807194-Chloro-3-(trifluoromethyl)benzenesulfonyl Chloride

Product 1

HCID 57942622HCID 57942622, compoundYield 46.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-amino-pyrazine-2-carboxylic acid methyl ester (153 mg, 1.0 mmol) in 2.0 mL of pyridine was added 4-chloro-3-trifluoromethyl-benzenesulfonyl chloride (279 mg, 1.0 mmol) in 1.0 mL of pyridine. The mixture was stirred at room temperature for 16 h, diluted with 15 mL of ethyl acetate, washed twice with 1M HCl (15 mL), dried on MgSO4 and the solvent was evaporated. The product was purified on silica gel column (15% ethyl acetate in hexane) to afford 185 mg of 3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyrazine-2-carboxylic acid methyl ester as white powder. MS: (M+H)/z=396.0.

Workup

  1. washwashed twice with 1M HCl (15 mL)
  2. customdried on MgSO4
  3. customthe solvent was evaporated
  4. customThe product was purified on silica gel column (15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-66069c46b4a64d5f8847c59fc74ea936
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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