Pyridine → HCID 59623721, compound

HRID 1093944Notes

Reaction equation

HRID 1093944 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]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=1[CH2:23][S:24](Cl)(=[O:26])=[O:25].N1C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][S:24]([CH2:23][C:14]2[CH:15]=[C:16]([C:19]([F:20])([F:21])[F:22])[CH:17]=[CH:18][C:13]=2[Cl:12])(=[O:26])=[O:25])=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 72669Methyl 3-aminopyrazinecarboxylateHCID 59623758HCID 59623758, compound

Product 1

HCID 59623721HCID 59623721, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-amino-pyrazine-2-carboxylic acid methyl ester (commercially available) (2.0 g) and (2-chloro-5-trifluoromethyl-phenyl)-methanesulfonyl chloride (Example 1.2) (4.2 g) in dichloromethane (32 ml) was added dropwise pyridine (5.3 ml) over a period of 5 minutes at ambient temperature. The reaction mixture was stirred at ambient temperature for 23 hours. Dichloromethane (50 ml) was added to the reaction mixture and the mixture was washed with aqueous sulfuric acid (2M) (3×30 ml). The phases were separated and the organic layer was concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/dichloromethane from 0:10 to 1:9) to give 3-(2-chloro-5-trifluoromethyl-phenylmethanesulfonylamino)-pyrazine-2-carboxylic acid methyl ester as a white solid (4.728 g). 1H-NMR (400 MHz, CDCl3): 10.30 (s, 1H), 8.59 (s, 1H), 8.47 (s, 1H), 7.77 (bs, 1H), 7.54-7.60 (m, 2H), 5.15 (s, 2H), 4.04 (s, 3H) ppm.

Workup

  1. washthe mixture was washed with aqueous sulfuric acid (2M) (3×30 ml)
  2. customThe phases were separated
  3. concentrationthe organic layer was concentrated
  4. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/dichloromethane from 0:10 to 1:9)

Sources & evidence

ORD record
ord-9108254a01f44c6d80a2e1ac3cf5d0e2
Source dataset
uspto-grants-2012_03
Patent number
US08133849B2

Reaction notes

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