tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylate → (S)-2-(4-{[(S)-Cyclobutyl-(3-fluoro-phenyl)-methyl]-carbamoyl}-8-fluoro-3-methyl-1-oxo-1H-isoquinolin-2-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 884759Notes

Reaction equation

HRID 884759 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:15]1([C@H:19]([NH:27][C:28]([CH:30]([C:34]2[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[C:35]=2[C:36](O)=[O:37])[C:31](=O)[CH3:32])=[O:29])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)[CH2:18][CH2:17][CH2:16]1>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][N:14]1[C:31]([CH3:32])=[C:30]([C:28](=[O:29])[NH:27][C@@H:19]([CH:15]2[CH2:16][CH2:17][CH2:18]2)[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)[C:34]2[C:35](=[C:39]([F:43])[CH:40]=[CH:41][CH:42]=2)[C:36]1=[O:37])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 1512533tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylateHCID 577333962-(1-{[(S)-cyclobutyl-(3-fluoro-phenyl)-methyl]-carbamoyl}-2-oxo-propyl)-6-fluoro-benzoic acid

Product 1

HCID 68407929(S)-2-(4-{[(S)-Cyclobutyl-(3-fluoro-phenyl)-methyl]-carbamoyl}-8-fluoro-3-methyl-1-oxo-1H-isoquinolin-2-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Procedure

(S)-2-Aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (510 mg, 2.54 mmol) and 2-(1-{[(S)-cyclobutyl-(3-fluoro-phenyl)-methyl]-carbamoyl}-2-oxo-propyl)-6-fluoro-benzoic acid (851 mg, 2.12 mmol) were condensed analogously to the method described for example 4 to give (S)-2-(4-{[(S)-Cyclobutyl-(3-fluoro-phenyl)-methyl]-carbamoyl}-8-fluoro-3-methyl-1-oxo-1H-isoquinolin-2-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester. The Boc-protection group was removed analogously to the method described for example 6 with trifluoroacetic acid in 1,2-dichloroethane to give the title compound. LC-MS (m/z) 466.3 (MH+); tR=0.96.

Workup

  1. customcondensed analogously to the method

Sources & evidence

ORD record
ord-7d12ca467b334382850e84664925564c
Source dataset
uspto-grants-2012_08
Patent number
US08242134B2

Reaction notes

Loading…