(E)-3-{2-[4-(1-tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridin-7-yl}-acrylic acid methyl ester → 3-{2-[4-(1-Tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridin-7-yl}-propionic acid methyl ester

HRID 872330Notes

Reaction equation

HRID 872330 reaction equation
[CH3:1][O:2][C:3](=[O:39])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[N:14]=[C:8]2[CH:7]=1>[Pd].CO>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[N:14]=[C:8]2[CH:7]=1

Participants

4

Reactant 1

HCID 66665952(E)-3-{2-[4-(1-tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridin-7-yl}-acrylic acid methyl ester

Product 1

HCID 666657493-{2-[4-(1-Tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridin-7-yl}-propionic acid methyl esterYield 46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (E)-3-{2-[4-(1-tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridin-7-yl}-acrylic acid methyl ester (450 mg, 0.86 mmol) and 10% palladium on carbon (0.2 g) in MeOH (20 mL) was stirred under a hydrogen atmosphere for 2 h, and the resulting mixture was filtered. The resulting solution was concentrated under reduced pressure. The remaining material was purified using MPLC (Biotage Isolera; 25 g SNAP cartridge: gradient from 100% hexane to 80% hexane/20% EtOAc over 1.0 min., 80% hexane/20% EtOAc for 3 min., gradient to 50% hexane/50% EtOAc over 3.5 min., 50% hexane/50% EtOAc for 14.6 min,) to give 3-{2-[4-(1-tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridin-7-yl}-propionic acid methyl ester (208 mg, 46%):

Workup

  1. filtrationthe resulting mixture was filtered
  2. concentrationThe resulting solution was concentrated under reduced pressure
  3. customThe remaining material was purified
  4. customMPLC (Biotage Isolera; 25 g SNAP cartridge: gradient from 100% hexane to 80% hexane/20% EtOAc over 1.0 min., 80% hexane/20% EtOAc for 3 min., gradient to 50% hexane/50% EtOAc over 3.5 min., 50% hexane/50% EtOAc for 14.6 min,)

Sources & evidence

ORD record
ord-16322997548e462eb14788c64293fae1
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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