3-Bromopropionamide → 3-{[(1R)-1-{4-chloro-2-fluoro-3-[(pyridin-3-yl)carbonyl]phenyl}propyl]amino}propanamide

HRID 2283424Notes

Reaction equation

HRID 2283424 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:11])[CH2:9][CH3:10])=[C:4]([F:12])[C:3]=1[C:13]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:14].Br[CH2:22][CH2:23][C:24]([NH2:26])=[O:25]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:11][CH2:22][CH2:23][C:24]([NH2:26])=[O:25])[CH2:9][CH3:10])=[C:4]([F:12])[C:3]=1[C:13]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:14]

Participants

3

Reactant 2

HCID 2335893-BromopropionamideHCID 89544767(1R)-1-{4-chloro-2-fluoro-3-[(pyridin-3-yl)carbonyl]phenyl}propan-1-amine

Product 1

HCID 895448283-{[(1R)-1-{4-chloro-2-fluoro-3-[(pyridin-3-yl)carbonyl]phenyl}propyl]amino}propanamideYield 0.8%

Procedure

(1R)-1-{4-chloro-2-fluoro-3-[(pyridin-3-yl)carbonyl]phenyl}propan-1-amine (0.1 g, 0.34 mmol) and 3-bromopropionamide (0.052 g, 0.34 mmol) heated in a microwave tube at 120° C., 150 W for 30 minutes. Reaction purified by Prep HPLC using Basic 0A3 system, followed by silica column (Biotage SP4) eluting 0-10% MeOH in EtOAc to give 3-{[(1R)-1-{4-chloro-2-fluoro-3-[(pyridin-3-yl)carbonyl]phenyl}propyl]amino}propanamide (0.001 g).

Workup

  1. customReaction
  2. custompurified by Prep HPLC
  3. washeluting 0-10% MeOH in EtOAc

Sources & evidence

ORD record
ord-7fa56b520c7d423bac9b40c956f87a9a
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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