HCID 178465852, compound → HCID 178465851, compound

HRID 1012127Notes

Reaction equation

HRID 1012127 reaction equation
C[O:2][C:3]([C:5]1[C:29]([O:30][CH2:31][CH3:32])=[CH:28][C:8]2[NH:9][C:10]([C:12]3[C:16]([NH:17][C:18](=[O:27])[C:19]4[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=4[F:26])=[CH:15][NH:14][N:13]=3)=[N:11][C:7]=2[CH:6]=1)=[O:4]>CO>[F:26][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([F:25])[C:19]=1[C:18]([NH:17][C:16]1[C:12]([C:10]2[NH:9][C:8]3[CH:28]=[C:29]([O:30][CH2:31][CH3:32])[C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=3[N:11]=2)=[N:13][NH:14][CH:15]=1)=[O:27]

Participants

3

Reactant 1

HCID 178465852HCID 178465852, compound

Product 1

HCID 178465851HCID 178465851, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-[4-(2,6-difluoro-benzoylamino)-1H-pyrazol-3-yl]-6-ethoxy-1H-benzimidazole-5-carboxylic acid methyl ester (90 mg) in MeOH-2M aqueous NaOH (1:1, 10 mL) was stirred at r.t. for 14 h. The MeOH was removed in vacuo and water (30 mL) added. The mixture was taken to pH=3 using 2M aqueous HCl and then extracted with EtOAc (×3). The combined organic extracts were reduced in vacuo and dried through azeotrope with toluene to give the title compound (72 mg) as a gray solid. (LC/MS: Rt 2.70, [M+H]+ 428.04).

Workup

  1. customThe MeOH was removed in vacuo and water (30 mL)
  2. additionadded
  3. extractionextracted with EtOAc (×3)
  4. dry with materialdried through azeotrope with toluene

Sources & evidence

ORD record
ord-1eee4809da3740629033ed15d757beb3
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

Loading…