6-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid → 6-Chloro-1H-pyrrolo [3.2-c]pyridine-2-carboxylic acid [1-(S)-(4-fluorobenzyl)-2-(3-(S)-hydroxypyrrolidin-1-yl)-2-oxoethyl]amide

HRID 751742Notes

Reaction equation

HRID 751742 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([C:11]([OH:13])=O)[NH:10][C:4]=2[CH:3]=1.Cl.[NH2:15][C@@H:16]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)[C:17]([N:19]1[CH2:23][CH2:22][C@H:21]([OH:24])[CH2:20]1)=[O:18]>>[F:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][C@H:16]([NH:15][C:11]([C:9]2[NH:10][C:4]3[CH:3]=[C:2]([Cl:1])[N:7]=[CH:6][C:5]=3[CH:8]=2)=[O:13])[C:17]([N:19]2[CH2:23][CH2:22][C@H:21]([OH:24])[CH2:20]2)=[O:18])=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 378189746-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acidHCID 672789012-(S)-amino-3-(4-fluorophenyl)-1-(3-(S)-hydroxypyrrolidin-1-yl)propan-1-one hydrochloride

Product 1

HCID 597536486-Chloro-1H-pyrrolo [3.2-c]pyridine-2-carboxylic acid [1-(S)-(4-fluorobenzyl)-2-(3-(S)-hydroxypyrrolidin-1-yl)-2-oxoethyl]amide

Procedure

The title compound was prepared as outlined in EXAMPLE 295 from 6-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid (Preparation 116) and 2-(S)-amino-3-(4-fluorophenyl)-1-(3-(S)-hydroxypyrrolidin-1-yl)propan-1-one hydrochloride (Preparation 103). The crude product was recrystallised from ethyl acetate to give the title compound. δH (CD3OD): 1.77–1.98 (2H, m), 3.08–3.88 (6H, 6 m), 4.30, 4.42 (1H, 2 m), 5.07, 5.09 (1H, 2m), 7.00 (2H, m), 7.30 (3H, m), 7.43 (1H, m), 8.67 (1H, s); m/z (ES+)=430.90 [M+H]+; RT=3.29 min.

Workup

  1. customThe title compound was prepared
  2. customThe crude product was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-17438838f1314739887d9c4566fe68a0
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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