4-Bromoaniline → HCID 67229890, compound

HRID 1406520Notes

Reaction equation

HRID 1406520 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:14][C:13]2[CH:15]=[C:16]([C:21](O)=[O:22])[C:17]([F:20])=[C:18]([F:19])[C:12]=2[N:11]=1.[Br:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1>C(OCC)(=O)C.C(#N)C>[Br:24][C:25]1[CH:31]=[CH:30][C:28]([NH:29][C:21]([C:16]2[C:17]([F:20])=[C:18]([F:19])[C:12]3[N:11]=[C:10]([NH:9][C:3]4[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=4[Cl:8])[NH:14][C:13]=3[CH:15]=2)=[O:22])=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 78074-BromoanilineHCID 67229875HCID 67229875, compound

Product 1

HCID 67229890HCID 67229890, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(2,6-Dichlorophenylamino)-4,5-difluoro-1H-benzimidazole-6-carboxylic acid (150 mg 0.42 mmol), TEA (0.15 mL, 1.05 mmol), 4-bromoaniline (70 mg, 0.42 mmol) and 50% solution of PPA (0.3 mL 0.5 mmol) in ethyl acetate in 10 mL acetonitrile was stirred for a weekend at ambient temperature. Then the solvent was removed i.vac. The residue was purified by HPLC.

Workup

  1. customThen the solvent was removed i.vac
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-b3edf08b9ccb4b69a9e402a3807dffa6
Source dataset
uspto-grants-2014_12
Patent number
US08916599B2

Reaction notes

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