HCID 59543644, compound → HCID 59543508, compound

HRID 1697693Notes

Reaction equation

HRID 1697693 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[C:21]([N:22]3[CH2:26][C@H:25]([S:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[C:36]([F:39])([F:38])[F:37])(=[O:29])=[O:28])[CH2:24][C@H:23]3[C:40](=[O:47])[NH:41][C:42]3([C:45]#[N:46])[CH2:44][CH2:43]3)=[CH:20][C:19]([CH3:48])=[N:18]2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>[Pd].C(O)C>[C:45]([C:42]1([NH:41][C:40]([C@@H:23]2[CH2:24][C@@H:25]([S:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:36]([F:39])([F:38])[F:37])(=[O:28])=[O:29])[CH2:26][N:22]2[C:21]2[N:17]([CH:14]3[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]3)[N:18]=[C:19]([CH3:48])[CH:20]=2)=[O:47])[CH2:43][CH2:44]1)#[N:46]

Participants

4

Reactant 1

HCID 59543644HCID 59543644, compound

Product 1

HCID 59543508HCID 59543508, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on charcoal 10% (5 mg) was added to a solution of 4-{5-[(2S,4R)-2-(1-cyano-cyclopropylcarbamoyl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidin-1-yl]-3-methyl-pyrazol-1-yl}-piperidine-1-carboxylic acid benzyl ester (12 mg, 18 umol; example 406c) in ethanol (1 ml). The reaction mixture was put under an hydrogen atmosphere and stirred at ambient temperature for 12 h. After filtration over dicalite the filtrate was brought to dryness to give the title compound (4.4 mg, 8 umol; 46%) as white solid. MS (ESI): m/z=551 [M+H]+.

Workup

  1. filtrationAfter filtration over dicalite the filtrate

Sources & evidence

ORD record
ord-a8d0267faf7445bf8f824177bb680e8c
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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