Acetic Anhydride → HCID 178502000, compound

HRID 1518048Notes

Reaction equation

HRID 1518048 reaction equation
[NH2:1][C:2]1[C:7]2[NH:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=3)=[N:10][C:6]=2[CH:5]=[C:4]([NH:18][C:19]([O:21][CH3:22])=[O:20])[CH:3]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>ClCCl>[C:23]([NH:1][C:2]1[C:7]2[NH:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=3)=[N:10][C:6]=2[CH:5]=[C:4]([NH:18][C:19]([O:21][CH3:22])=[O:20])[CH:3]=1)(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178501999HCID 178501999, compound

Product 1

HCID 178502000HCID 178502000, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-amino-5-(methoxycarbonyl)amino-2-(4-bromophenyl)-1H-benzo[d]-imidazole (60 mg, 0.17 mmol) in dichloromethane (5 mL) was added acetic anhydride (18 mg, 0.17 mmol) and the solution was stirred at room temperature for 3 h. The reaction mixture was concentrated in vacuo and purified by column chromatography on silica gel using hexane/EtOAc (4/1) as the eluant to afford the desired product (55 mg, 80%) as a pale yellow powder: 1H-NMR (300 MHz, CD3OD) δ 2.24 (s, 3H), 3.74 (s, 3H), 7.65 (m, 3H), 7.67 (bs, 1H), 7.90 (m, 2H); ESI MS m/z 403.0 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-135b26e731ad45a9882789d8a44d46c3
Source dataset
uspto-grants-2012_07
Patent number
US08232410B2

Reaction notes

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