Dicyclohexylcarbodiimide → N-{4-[(3,5-Dimethyl-4-{[(2-methylpropane-2-sulfonyl)carbamoyl]methyl}-1H-pyrazol-1-yl)methyl]phenyl}-4-(trifluoromethyl)benzamide

HRID 1631916Notes

Reaction equation

HRID 1631916 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][C:8](O)=[O:9])=[C:5]([CH3:11])[N:4]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:31])[C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)[N:3]=1.[CH3:32][C:33]([S:36]([NH2:39])(=[O:38])=[O:37])([CH3:35])[CH3:34].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][C:2]1[C:6]([CH2:7][C:8](=[O:9])[NH:39][S:36]([C:33]([CH3:35])([CH3:34])[CH3:32])(=[O:38])=[O:37])=[C:5]([CH3:11])[N:4]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:31])[C:21]3[CH:22]=[CH:23][C:24]([C:27]([F:29])([F:28])[F:30])=[CH:25][CH:26]=3)=[CH:15][CH:14]=2)[N:3]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 2757335tert-ButylsulfonamideHCID 58071835{3,5-Dimethyl-1-[4-(4-trifluoromethyl-benzoylamino)-benzyl]-1H-pyrazol-4-yl}-acetic acid

Product 1

HCID 58071686N-{4-[(3,5-Dimethyl-4-{[(2-methylpropane-2-sulfonyl)carbamoyl]methyl}-1H-pyrazol-1-yl)methyl]phenyl}-4-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

{3,5-Dimethyl-1-[4-(4-trifluoromethyl-benzoylamino)-benzyl]-1H-pyrazol-4-yl}-acetic acid (example 1.1, 250 mg, 0.58 mmol), 2-methylpropane-2-sulfonamide (95 mg, 0.70 mmol), 1,3-dicyclohexylcarbodiimid (143 mg, 0.70 mmol) and 4-dimethylaminopyridine (85 mg, 0.70 mmol) in 2.5 ml dichloromethane were stirred for 3 h at 30° C. The solvent was removed under reduced pressure and the residue was purified by MPLC (silica gel, CH2Cl2/methanol 95:5).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by MPLC (silica gel, CH2Cl2/methanol 95:5)

Sources & evidence

ORD record
ord-a97462f9289c44bbad1ac07bee032a45
Source dataset
uspto-grants-2014_07
Patent number
US08791272B2

Reaction notes

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