4-(2-Methoxyethoxy)piperidine hydrochloride → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid {1-(S)-(4-fluorobenzyl)-2-[4-(2-methoxyethoxy)piperidin-1-yl]-2-oxoethyl}amide

HRID 1693470Notes

Reaction equation

HRID 1693470 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.Cl.[CH3:27][O:28][CH2:29][CH2:30][O:31][CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>>[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][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])[C:15]([N:35]2[CH2:36][CH2:37][CH:32]([O:31][CH2:30][CH2:29][O:28][CH3:27])[CH2:33][CH2:34]2)=[O:16])=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 220613544-(2-Methoxyethoxy)piperidine hydrochlorideHCID 597536992-(S)-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)propionic acid

Product 1

HCID 597535705-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid {1-(S)-(4-fluorobenzyl)-2-[4-(2-methoxyethoxy)piperidin-1-yl]-2-oxoethyl}amide

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-(2-methoxyethoxy)piperidine hydrochloride (Preparation 82). Purification by chromatography using dichloromethane/methanol (95:5) as the eluent gave the title compound as an off-white powder. m/z (ES+) 503.26 [M+H]+; RT=3.3 min.

Workup

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

Sources & evidence

ORD record
ord-87d13f989ced4e6da717ab9f994f6c89
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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