Ethanol → HCID 57989697, compound

HRID 1671182Notes

Reaction equation

HRID 1671182 reaction equation
[CH3:1][C:2]([C:5]1[S:6][C:7]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([CH:35]=[CH2:36])[N:30]=2)=[C:8]([C:10]2[C:11]([F:28])=[C:12]([NH:16][S:17]([C:20]3[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=3[F:27])(=[O:19])=[O:18])[CH:13]=[CH:14][CH:15]=2)[N:9]=1)([CH3:4])[CH3:3].[CH3:37][S:38]([OH:40])=[O:39].[Na].C(O)C>C(O)(=O)C.O>[CH3:4][C:2]([C:5]1[S:6][C:7]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([CH2:35][CH2:36][S:38]([CH3:37])(=[O:40])=[O:39])[N:30]=2)=[C:8]([C:10]2[C:11]([F:28])=[C:12]([NH:16][S:17]([C:20]3[C:21]([F:27])=[CH:22][CH:23]=[CH:24][C:25]=3[F:26])(=[O:19])=[O:18])[CH:13]=[CH:14][CH:15]=2)[N:9]=1)([CH3:1])[CH3:3]

Participants

7

Reactant 4

HCID 702EthanolHCID 87251Methanesulfinic acidHCID 5360545SodiumHCID 57989882HCID 57989882, compound

Product 1

HCID 57989697HCID 57989697, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

N-{3-[2-(1,1-dimethylethyl)-5-(2-ethenyl-4-pyrimidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide (0.15 g, 0.283 mmol) and methane sulfinic acid, sodium salt (0.144 g, 1.414 mmol) were stirred in acetic acid (1.5 ml) and ethanol (1.5 ml) at RT in a screw-top vial overnight. The reaction mixture is diluted with water and extracted 2× with EtOAc. The EtOAc is washed with brine, dried over MgSO4, filtered, and concentrated. The crude mixture was placed on silica gel and chromatography (0 to 80% DCM/EtOAc, gradient) to obtain the title compound (173 mg, 81%). 1H NMR (400 MHz, DMSO-d6) ppm 10.87 (s, 1H), 8.54 (d, J=5.31 Hz, 1H), 7.68 (ddd, J=14.56, 8.42, 6.13 Hz, 1H), 7.43 (t, J=7.32 Hz, 2H), 7.32 (t, J=7.97 Hz, 1H), 7.23 (t, J=9.06 Hz, 2H), 6.75 (d, J=5.31 Hz, 1H), 3.53 (m, 2H), 3.29 (m, 2H), 3.03 (s, 3H), 1.44 (m, 9H); MS (ESI): 611 [M+H]+.

Workup

  1. extractionextracted 2× with EtOAc
  2. washThe EtOAc is washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-552208b4ff8d4470a36c75aa4540c217
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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