Propyl mercaptan → Methyl 4-[4-(cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate

HRID 1799389Notes

Reaction equation

HRID 1799389 reaction equation
[CH2:1]([SH:4])[CH2:2][CH3:3].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl[C:16]1[N:20]([C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=2)[N:19]=[CH:18][C:17]=1[C:31](=[O:39])[NH:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>CN(C=O)C.C1COCC1.C(OCC)(=O)C>[CH:33]1([NH:32][C:31]([C:17]2[CH:18]=[N:19][N:20]([C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=3)[C:16]=2[S:4][CH2:1][CH2:2][CH3:3])=[O:39])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

7

Reactant 3

HCID 7848Propyl mercaptanHCID 2724254Sodium bis(trimethylsilyl)amideHCID 57437896Methyl 4-[5-chloro-4-(cyclohexylcarbamoyl)pyrazol-1-yl]benzoate2×

Product 1

HCID 57857095Methyl 4-[4-(cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Propane thiol (88 mg, 1.16 mmol) was dissolved in DMF (5 mL) and treated at ambient temperature with a 1M solution of NaHMDS in THF (1.16 mL). After stirring for 15 min the clear solution was added to a suspension of methyl 4-[5-chloro-4-(cyclohexylcarbamoyl)pyrazol-1-yl]benzoate (Intermediate #15) (378 mg, 1.05 mmol) in DMF (10 mL). Stirring was continued at ambient temperature for 2 h and then the reaction mixture was diluted with ethyl acetate (100 mL), washed with water (4×25 mL) and dried (MgSO4). Volatiles were removed by evaporation under reduced pressure to give a clear oil which was purified by chromatography on silica gel, eluting with an ethyl acetate/hexane gradient (0-50%) to give the title compound as a white solid. (363 mg, 86%)

Workup

  1. stirringStirring
  2. waitwas continued at ambient temperature for 2 h
  3. washwashed with water (4×25 mL)
  4. dry with materialdried (MgSO4)
  5. customVolatiles were removed by evaporation under reduced pressure
  6. customto give a clear oil which
  7. customwas purified by chromatography on silica gel
  8. washeluting with an ethyl acetate/hexane gradient (0-50%)

Sources & evidence

ORD record
ord-a7bc87b88a7f425faeacc8fb5aef976d
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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