Methanol → HCID 86606868, compound

HRID 1991083Notes

Reaction equation

HRID 1991083 reaction equation
[C:1]([C@@H:4]1[CH2:9][N:8]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH2:7][CH2:6][N:5]1[C:18](=[O:32])/[CH:19]=[CH:20]/[C:21]1C=CC(Cl)=C[C:22]=1[NH:28]C(=O)C)(=O)[CH3:2].[ClH:33].[NH2:34][OH:35].C[OH:37]>>[Cl:33][CH:7]1[CH2:6][N:5]([C:18](=[O:32])/[CH:19]=[CH:20]/[CH2:21][C:22]([NH2:28])=[O:37])[C@H:4]([C:1](=[N:34][OH:35])[CH3:2])[CH2:9][N:8]1[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 11753883HCID 11753883, compound

Product 1

HCID 86606868HCID 86606868, compoundYield 12%

Procedure

N-(2-{(E)-3-[(S)-2-Acetyl-4-(4-fluoro-benzyl)-piperazin-1-yl]-3-oxo-propenyl}-5-chloro-phenyl)-acetamide (250 mg, 0.55 mmol) was dissolved in 8 ml MeOH and 83.5 mg (1.2 mmol) hydroxylamine hydrochloride were added. This mixture was stirred under reflux for 16 hours and then evaporated. The title compound was purified by chromatography (SiO2, ethyl acetate/MeOH/NH3conc. 95/5/0.5) and was isolated as a pale solid (30 mg, 12%)

Workup

  1. temperatureunder reflux for 16 hours
  2. customevaporated
  3. customThe title compound was purified by chromatography (SiO2, ethyl acetate/MeOH/NH3conc. 95/5/0.5)

Sources & evidence

ORD record
ord-bbbba2f6d19940ffa9fed169c3ca56fa
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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