Propyl mercaptan → Methyl 3-[4-(cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate

HRID 1799390Notes

Reaction equation

HRID 1799390 reaction equation
[CH2:1]([SH:4])[CH2:2][CH3:3].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1COCC1.Cl[C:21]1[N:25]([C:26]2[CH:27]=[C:28]([CH:33]=[CH:34][CH:35]=2)[C:29]([O:31][CH3:32])=[O:30])[N:24]=[CH:23][C:22]=1[C:36](=[O:44])[NH:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>CN(C=O)C.C(OCC)(=O)C>[CH:38]1([NH:37][C:36]([C:22]2[CH:23]=[N:24][N:25]([C:26]3[CH:27]=[C:28]([CH:33]=[CH:34][CH:35]=3)[C:29]([O:31][CH3:32])=[O:30])[C:21]=2[S:4][CH2:1][CH2:2][CH3:3])=[O:44])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

7

Reactant 4

HCID 7848Propyl mercaptanHCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 57437897Methyl 3-[5-chloro-4-(cyclohexylcarbamoyl)pyrazol-1-yl]benzoate2×

Product 1

HCID 57857096Methyl 3-[4-(cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Propane thiol (48 mg, 0.57 mmol) was dissolved in DMF (3 mL) and treated at ambient temperature with a 1M solution of NaHMDS in THF (0.63 mL, 0.63 mmol). After stirring for 15 min a solution of methyl 3-[5-chloro-4-(cyclohexylcarbamoyl)pyrazol-1-yl]benzoate (Intermediate #19) (205 mg, 0.57 mmol) in DMF (5 mL) was added and stirring continued for 2 h. Ethyl acetate (50 mL) was added and the mixture washed with water (3×20 mL), dried (MgSO4) and evaporated to give an oil which was purified by chromatography on silica gel eluting with an EtOAc/DCM gradient (0-25%) to provide the title compound as a clear colourless oil. (175 mg, 75%)

Workup

  1. additionwas added
  2. washthe mixture washed with water (3×20 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give an oil which
  6. customwas purified by chromatography on silica gel eluting with an EtOAc/DCM gradient (0-25%)

Sources & evidence

ORD record
ord-d010747a7f12481597a6d94f692c9808
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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