Acetic Acid → HCID 20740234, compound

HRID 1883155Notes

Reaction equation

HRID 1883155 reaction equation
[C:1]([C@@H:3]([NH:14][C:15]([C@@H:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@@H:18]1[NH:23][C:24]([C:26]1[N:27]([CH3:35])[C:28]2[C:33]([CH:34]=1)=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])=[O:16])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1)#[N:2].C(O)(=O)C>C(OCC)(=O)C>[NH2:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][C@H:3]([NH:14][C:15]([C@@H:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C@@H:18]2[NH:23][C:24]([C:26]2[N:27]([CH3:35])[C:28]3[C:33]([CH:34]=2)=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[O:16])[C:1]#[N:2])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 60083681HCID 60083681, compound

Product 1

HCID 20740234HCID 20740234, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 120 mg (0.25 mmol) of 1-methyl-1H-indole-2-carboxylic acid ((1S,2R)-2-{[(S)-cyano-(4-nitro-benzyl)-methyl]-carbamoyl}-cyclohexyl)-amide dissolved in 5 mL ethyl acetate was added 20 mg activated carbon on charcoal (10% Wt.) and 0.7 mL glacial acetic acid. The reaction mixture was hydrogenated under normal atmosphere (H2 balloon) for two hours, filtered through a cake of celite, washed with water and 10% NaOH aqueous solution, dried over magnesium sulfate, and concentrated to provide 80 mg of 1-methyl-1H-indole-2-carboxylic acid ((1S,2R)-2-{[(S)-(4-amino-benzyl)-cyano-methyl]-carbamoyl}-cyclohexyl)-amide. HPLC: 92% pure, yield: 71%, MS: 444 (M+H+).

Workup

  1. additionwas added 20 mg
  2. filtrationfiltered through a cake of celite
  3. washwashed with water and 10% NaOH aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6e45a743a7e740fcb69dfe47a6c323db
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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