Trifluoroacetic acid → (4-amino-piperidin-1-yl)-[(4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazol-1-yl]-methanone

HRID 1894513Notes

Reaction equation

HRID 1894513 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([N:16]2[C@@:20]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)([CH3:21])[C@@:19]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)([CH3:29])[N:18]=[C:17]2[C:37]2[CH:38]=[N:39][C:40]([C:46]([CH3:49])([CH3:48])[CH3:47])=[CH:41][C:42]=2[O:43][CH2:44][CH3:45])=[O:15])[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:14]([N:16]2[C@@:20]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)([CH3:21])[C@@:19]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)([CH3:29])[N:18]=[C:17]2[C:37]2[CH:38]=[N:39][C:40]([C:46]([CH3:47])([CH3:49])[CH3:48])=[CH:41][C:42]=2[O:43][CH2:44][CH3:45])=[O:15])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57670115{1-[(4S,5R)-2-(6-tert-Butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl]-piperidin-4-yl}-carbamic acid tert-butyl ester

Product 1

HCID 57669927(4-amino-piperidin-1-yl)-[(4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazol-1-yl]-methanoneYield 91.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {1-[(4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl]-piperidin-4-yl}-carbamic acid tert-butyl ester (220 mg, 0.304 mmole, example 203) in dichloromethane (6 mL) was treated with trifluoroacetic acid (6 mL) at 0° C. and allowed to stir for 2 h before concentrated to dryness under reduced pressure. The residue was then taken up in dichloromethane (100 mL), washed with aqueous sodium carbonate (2×15 mL), water (15 mL) and concentrated to give the title compound (174 mg). HR-MS (ES, m/z) calculated for C34H42Cl2N5O2 [(M+H)+] 622.2710, observed 622.2714.

Workup

  1. concentrationbefore concentrated to dryness under reduced pressure
  2. washwashed with aqueous sodium carbonate (2×15 mL), water (15 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-30aa630e95384f36a5c36f90d99cbabb
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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