Trifluoroacetic acid → HCID 20740221, compound

HRID 1883140Notes

Reaction equation

HRID 1883140 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]([C:38]#[N:39])[NH:16][C:17]([C@@H:19]2[CH2:24][CH2:23][CH2:22][CH2:21][C@@H:20]2[NH:25][C:26]([C:28]2[N:29]([CH3:37])[C:30]3[C:35]([CH:36]=2)=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])=[O:18])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:38]([CH:15]([NH:16][C:17]([C@@H:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C@@H:20]1[NH:25][C:26]([C:28]1[N:29]([CH3:37])[C:30]2[C:35]([CH:36]=1)=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])=[O:18])[CH2:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)#[N:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 60083657HCID 60083657, compound

Product 1

HCID 20740221HCID 20740221, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[2-cyano-2-({(1R,2S)-2-[(1-methyl-1H-indole-2-carbonyl)-amino]-cyclohexanecarbonyl}-amino)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester (1.20 g, 2.24 mmol) in 20 mL of CH2Cl2, was added TFA (4.0 mL, 52 mmol). The reaction mixture was stirred at ambient temperature for 4 hours, concentrated, poured into an aqueous sodium bicarbonate solution, extracted with ethyl acetate, dried with sodium sulfate, and concentrated to give 541 mg (55%) of 1-methyl-1H-indole-2-carboxylic acid {(1S,2R)-2-[(cyano-piperidin-4-ylmethyl-methyl)-carbamoyl]-cyclohexyl}-amide as a pale-yellow amorphous material. MS: 436 (M+H+).

Workup

  1. concentrationconcentrated
  2. additionpoured into an aqueous sodium bicarbonate solution
  3. extractionextracted with ethyl acetate
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f4b6942b94e04aeba9bf8a2df9937321
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

Loading…