Sodium methanethiolate → HCID 118049844, compound

HRID 595866Notes

Reaction equation

HRID 595866 reaction equation
CS(O[C@H:6]1[CH2:11][CH2:10][CH2:9][C@@H:8]([C:12]2[CH:17]=[N:16][C:15]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[C:14]([C:25]3[CH:30]=[CH:29][C:28]([C:31](=[O:40])[NH:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[C:27]([F:41])[CH:26]=3)[N:13]=2)[CH2:7]1)(=O)=O.[CH3:42][S-:43].[Na+]>CO>[CH2:33]([NH:32][C:31](=[O:40])[C:28]1[CH:29]=[CH:30][C:25]([C:14]2[C:15]([NH:18][C:19](=[O:24])[C:20]([CH3:21])([CH3:23])[CH3:22])=[N:16][CH:17]=[C:12]([C@@H:8]3[CH2:9][CH2:10][CH2:11][C@@H:6]([S:43][CH3:42])[CH2:7]3)[N:13]=2)=[CH:26][C:27]=1[F:41])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 118051738HCID 118051738, compound

Product 1

HCID 118049844HCID 118049844, compoundYield 108.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (+/−)-(1S,3R)-3-(6-(4-(benzylcarbamoyl)-3-fluorophenyl)-5-pivalamidopyrazin-2-yl)cyclohexyl methanesulfonate (25 mg, 0.043 mmol) and sodium methanethiolate (24.09 mg, 0.344 mmol) in MeOH (430 μL) was heated at 80° C. for 2 h. Solvent was removed and the residue was purified with flash chromatography eluting with EtOAc (containing 10% of MeOH)/heptane to provide 25 mg of crude (+/−)-N-benzyl-2-fluoro-4-(6-((1R,3R)-3-(methylthio)cyclohexyl)-3-pivalamidopyrazin-2-yl)benzamide which was taken to the next step without further purification. LCMS (m/z): 535.3 (MH+), 1.09 min.

Workup

  1. customSolvent was removed
  2. customthe residue was purified with flash chromatography
  3. washeluting with EtOAc (containing 10% of MeOH)/heptane

Sources & evidence

ORD record
ord-56fb5343307048e0a26f101e0e7492f6
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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