tert-Butyl 4-(methylamino)piperidine-1-carboxylate → 4-{[2-(S)-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)propionyl]methylamino}piperidine-1-carboxylic acid tert-butyl ester

HRID 1693473Notes

Reaction equation

HRID 1693473 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11]([NH:13][C@@H:14]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C:15](O)=[O:16])=[O:12])[NH:8][C:5]2=[CH:6][N:7]=1.[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([NH:39][CH3:40])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>>[C:26]([O:30][C:31]([N:33]1[CH2:34][CH2:35][CH:36]([NH:39][CH2:40][C:15](=[O:16])[C@@H:14]([NH:13][C:11]([C:9]2[NH:8][C:5]3=[CH:6][N:7]=[C:2]([Cl:1])[CH:3]=[C:4]3[CH:10]=2)=[O:12])[CH2:18][C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[CH2:37][CH2:38]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]

Participants

3

Reactant 2

HCID 15380702tert-Butyl 4-(methylamino)piperidine-1-carboxylateHCID 597536992-(S)-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)propionic acid

Product 1

HCID 866017704-{[2-(S)-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)propionyl]methylamino}piperidine-1-carboxylic acid tert-butyl ester

Procedure

The title compound was prepared according to EXAMPLE 229 from 2-(S)-[(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)-propionic acid (EXAMPLE 228) and 4-methylaminopiperidine-1-carboxylic acid tert-butyl ester (Preparation 86). Purification by chromatography using dichloromethane/methanol (95:5) as the eluent gave the title compound as a pale yellow powder. m/z (ES+)=558.48 [M+H]+; RT=3.82 min.

Workup

  1. customThe title compound was prepared
  2. customPurification by chromatography

Sources & evidence

ORD record
ord-b7ff63c9acbd4013849b1b29dbc63e25
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

Loading…