HCID 59366875, compound → HCID 59367253, compound

HRID 1923997Notes

Reaction equation

HRID 1923997 reaction equation
C(OC([NH:11][CH:12]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][C@H:20]([NH:49][C:50](=[O:56])[O:51][C:52]([CH3:55])([CH3:54])[CH3:53])[C:21](=[O:48])[NH:22][C@@H:23]([C:35](=[O:47])[NH:36][C:37]2[CH:38]=[N:39][C:40]3[C:45]([CH:46]=2)=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)[CH2:13]1)=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][CH:12]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][C@H:20]([NH:49][C:50](=[O:56])[O:51][C:52]([CH3:54])([CH3:53])[CH3:55])[C:21](=[O:48])[NH:22][C@@H:23]([C:35](=[O:47])[NH:36][C:37]2[CH:38]=[N:39][C:40]3[C:45]([CH:46]=2)=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:27][CH:26]=2)[CH2:13]1

Participants

4

Reactant 1

HCID 59366875HCID 59366875, compound

Product 1

HCID 59367253HCID 59367253, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl N-[(1S)-4-(3-{[(benzyloxy)carbonyl]amino}pyrrolidin-1-yl)-1-{[(1R)-1-[(quinolin-3-yl)carbamoyl]-2-[4-(trifluoromethyl)phenyl]ethyl]carbamoyl}butyl]carbamate CXIII (170 mg, 0.22 mmol) in methanol (20 mL) was added catalytic amount of 10% Pd/C catalyst. The mixture was hydrogenated at normal pressure for 48 h. The catalyst was filtered through Celite and the filtrate was concentrated to give tert-butyl N-[(1S)-4-(3-aminopyrrolidin-1-yl)-1-{[(1R)-1-[(quinolin-3-yl)carbamoyl]-2-[4-(trifluoromethyl)phenyl]ethyl]carbamoyl}butyl]carbamate CXIV (120 mg, 0.19 mmol, 86.4% yield). ESIMS found for C33H41N6O4F3 m/z 643 (M+H).

Workup

  1. filtrationThe catalyst was filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9e1e7ce9f3904132b6259ffd92faf1bc
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

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