Hydroxylamine → 6-[2-(4-Phenyl-piperazin-1-yl)-acetylamino]-benzo[b]thiophene-2-carboxylic acid hydroxyamide

HRID 545466Notes

Reaction equation

HRID 545466 reaction equation
CO[C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([NH:14][C:15](=[O:18])[CH2:16]Cl)[CH:12]=[CH:13][C:7]=2[CH:6]=1)=[O:4].[NH2:19][OH:20].[CH3:21][N:22]([CH:24]=O)[CH3:23]>>[OH:20][NH:19][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([NH:14][C:15](=[O:18])[CH2:16][N:14]3[CH2:15][CH2:24][N:22]([C:23]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:3]=4)[CH2:21][CH2:11]3)[CH:12]=[CH:13][C:7]=2[CH:6]=1)=[O:4]

Participants

4

Reactant 3

HCID 787HydroxylamineHCID 6228DimethylformamideHCID 595564046-(2-Chloro-acetylamino)-benzo[b]thiophene-2-carboxylic acid methyl ester

Product 1

HCID 589688786-[2-(4-Phenyl-piperazin-1-yl)-acetylamino]-benzo[b]thiophene-2-carboxylic acid hydroxyamide

Conditions

Temperature
50 °C

Procedure

To a solution of 6-(2-chloro-acetylamino)-benzo[b]thiophene-2-carboxylic acid methyl ester (75 mg, 0.26 mmol) in DMF (2 mL) was added amine (85.8 mg, 0.52 mmol). The reaction mixture was heated to 50° C. After 24 h, NH2OH (50% aq., 1 mL) was added to the solution. The solution was stirred until the disappearance of starting material. After removal of solvent, MeOH/H2O was added until a precipitate forms. The solid was filtered yielding the desired amide. 1H NMR (DMSO-d6) δ 11.32 (br s, 1H), 9.97 (s, 1H), 9.28 (br s, 1H), 8.39 (s, 1H), 7.85-7.72 (m, 2H), 7.55 (d, J=7.0 Hz, 1H), 7.24-7.10 (m, 2H), 6.94-6.84 (m, 2H), 6.72 (t, J=7.0 Hz, 1H), 3.24-3.05 (m, 5H), 2.70-2.58 (m, 4H). MS (EI): cal'd (MH+) 411.14, exp (MH+) 411.33.

Workup

  1. customAfter removal of solvent, MeOH/H2O
  2. additionwas added until a precipitate forms
  3. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-8af6aab1811942feac958ecbd8d9caf3
Source dataset
uspto-grants-2011_05
Patent number
US07935724B2

Reaction notes

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