HCID 178451925, compound → HCID 178451923, compound

HRID 2273044Notes

Reaction equation

HRID 2273044 reaction equation
C(OC([NH:11][CH:12]1[CH2:15][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[N:23]=[C:24]([C@@H:27]4[CH2:31][CH2:30][CH2:29][N:28]4[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[NH:25][CH:26]=3)=[CH:18][CH:17]=2)[CH2:13]1)=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][CH:12]1[CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[N:23]=[C:24]([C@@H:27]4[CH2:31][CH2:30][CH2:29][N:28]4[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[NH:25][CH:26]=3)=[CH:18][CH:17]=2)[CH2:15]1

Participants

4

Reactant 1

HCID 178451925HCID 178451925, compound

Product 1

HCID 178451923HCID 178451923, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-tert-butyl 2-(4-(4-(3-(benzyloxycarbonylamino) cyclobutyl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (A8) (449 mg, 0.87 mmol) in methanol (10 mL) was added 10% Pd/C (50 mg) and the mixture was stirred overnight under H2 atmosphere in a balloon. The mixture was filtrated and concentrated to obtain the crude product (S)-tert-butyl 2-(4-(4-(3-aminocyclobutyl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (A9) (330 mg, 99% yield) without further purification.

Workup

  1. filtrationThe mixture was filtrated
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-859465a372e248aa975be67ccf862252
Source dataset
uspto-grants-2015_09
Patent number
US09120779B2

Reaction notes

Loading…