Ammonia → HCID 89690958, compound

HRID 2202922Notes

Reaction equation

HRID 2202922 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:14]3[CH:15]=[CH:16][C:17]4[N:21]=[C:20]([CH:22]5[CH2:24][CH:23]5[C:25]([OH:27])=O)[N:19]([CH3:28])[C:18]=4[CH:29]=3)[C:10](=[O:30])[CH:9]=2)=[CH:4][CH:3]=1.C([N:35](CC)CC)C.ClC(OCC)=O.N>CC(C)=O>[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:14]3[CH:15]=[CH:16][C:17]4[N:21]=[C:20]([CH:22]5[CH2:24][CH:23]5[C:25]([NH2:35])=[O:27])[N:19]([CH3:28])[C:18]=4[CH:29]=3)[C:10](=[O:30])[CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 89691090HCID 89691090, compound

Product 1

HCID 89690958HCID 89690958, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (1RS,2RS)-2-(6-(4-((4-chlorobenzyl)oxy)-2-oxopyridin-1(2H)-yl)-1-methyl-1H-benzimidazol-2-yl)cyclopropanecarboxylic acid (150 mg) and triethylamine (0.139 ml) in acetone (2 ml) was added ethyl chloroformate (0.096 ml) at 0° C. The mixture was stirred at 0° C. for 1 h and then NH3 solution (0.101 ml) was added dropwise. The reaction mixture was stirred at room temperature for 3 h and then concentrated in vacuo. The residue was purified by silica gel chromatography (MeOH/EtOAc) to give the title compound (125 mg) as a white solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel chromatography (MeOH/EtOAc)

Sources & evidence

ORD record
ord-808cd71120c14e40adb3e928e5c11a66
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

Loading…