HCID 178445906, compound → HCID 178445907, compound

HRID 1883124Notes

Reaction equation

HRID 1883124 reaction equation
[C:1]([C@@H:3]([NH:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]1[NH:17][C:18]([C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][N:24]=[C:23]2[C:29]#[C:30][CH2:31][N:32]([CH3:34])[CH3:33])=[O:19])=[O:10])[CH2:4][CH:5]([CH3:7])[CH3:6])#[N:2]>CO.[Pd].C([O-])([O-])=O.[Ca+2]>[C:1]([C@@H:3]([NH:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]1[NH:17][C:18]([C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][N:24]=[C:23]2[CH2:29][CH2:30][CH2:31][N:32]([CH3:33])[CH3:34])=[O:19])=[O:10])[CH2:4][CH:5]([CH3:7])[CH3:6])#[N:2]

Participants

4

Reactant 1

HCID 178445906HCID 178445906, compound

Product 1

HCID 178445907HCID 178445907, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 12000666Calcium Palladium CarbonateCatalystHCID 887MethanolSolvent

Procedure

3-(3-dimethylamino-prop-1-ynyl)-1H-indazole-5-carboxylic acid [(1S,2R)-2-((S)-1-cyano-3-methyl-butylcarbamoyl)cyclohexyl]-amide (7 mg) was stirred with 5 mg 10% Pd/CaCO3 in methanol under hydrogen (balloon). After two hours at room temperature the mixture was degassed with nitrogen, filtered through celite to remove the catalyst and the solution concentrated to give 7 mg of 3-(3-dimethylamino-propyl)-1H-indazole-5-carboxylic acid [(1S,2R)-2-((S)-1-cyano-3-methyl-butylcarbamoyl)cyclohexyl]-amide.

Workup

  1. customAfter two hours at room temperature the mixture was degassed with nitrogen
  2. filtrationfiltered through celite
  3. customto remove the catalyst
  4. concentrationthe solution concentrated

Sources & evidence

ORD record
ord-cdf9792eaab54ce29d352fb5e57dc1a1
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

Loading…