Acetic Anhydride → HCID 20740210, compound

HRID 1883141Notes

Reaction equation

HRID 1883141 reaction equation
Cl.[C:2]([CH:4]([NH:12][C:13]([C@@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]1[NH:21][C:22]([C:24]1[N:25]([CH3:33])[C:26]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])=[O:14])[CH2:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)#[N:3].[C:34](OC(=O)C)(=[O:36])[CH3:35]>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:34]([N:9]1[CH2:10][CH2:11][CH:6]([CH2:5][CH:4]([NH:12][C:13]([C@@H:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C@@H:16]2[NH:21][C:22]([C:24]2[N:25]([CH3:33])[C:26]3[C:31]([CH:32]=2)=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[O:14])[C:2]#[N:3])[CH2:7][CH2:8]1)(=[O:36])[CH3:35]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 86591896HCID 86591896, compound

Product 1

HCID 20740210HCID 20740210, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-methyl-1H-indole-2-carboxylic acid {(1S,2R)-2-[(cyano-piperidin-4-ylmethyl-methyl)-carbamoyl]-cyclohexyl}-amide hydrochloride (0.50 g, 1.06 mmol) in 2 mL of DMF, was added 0.5 mL of TEA, acetic anhydride (0.15 mL, 1.59 mmol), and a few crystals of DMAP. The reaction mixture was stirred at ambient temperature for 1 hour, and partitioned between 50 mL of water and 50 mL of ethyl acetate. The separated organic layer was washed with water (2×50 mL), dried with sodium sulfate, filtered, concentrated, and purified by column chromatography (5:95, MeOH/CH2Cl2) to give 165 mg (33%) of 1-methyl-1H-indole-2-carboxylic acid ((1S,2R)-2-{[(1-acetyl-piperidin-4-ylmethyl)-cyano-methyl]-carbamoyl}-cyclohexyl)-amide as a white amorphous solid. MS: 478 (M+H+).

Workup

  1. custompartitioned between 50 mL of water and 50 mL of ethyl acetate
  2. washThe separated organic layer was washed with water (2×50 mL)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography (5:95, MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-e14fb3d9d719472794f800b738363206
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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