Water → HCID 57917705, compound

HRID 1878326Notes

Reaction equation

[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=3)[C:18]([NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:37](Cl)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.O>ClCCl>[C:37]([NH:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=3)[C:18]([NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-((4-(4-Aminobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (0.203 mmol, 0.080 g) and triethylamine (1.015 mmol, 0.103 g) were dissolved in dichloromethane (12 mL) and the stirred mixture was cooled to 0° C. Benzoyl chloride (0.305 mmol, 0.043 g) was added and the reaction mixture was allowed to reach room temperature and stir overnight. Water was added to the reaction and the organic layer was then separated, dried (sodium sulfate) and concentrated under vacuum. The residue was purified by silica column chromatography (dichloromethane/methanol (5% to 10%)) and coevaporated with dichloromethane (×3) and diethyl ether (×3) to give the title compound (93 mg). MS (ESI) m/z 499.8 [M+H]+

Workup

customto reach room temperature
customthe organic layer was then separated
dry with materialdried (sodium sulfate)
concentrationconcentrated under vacuum
customThe residue was purified by silica column chromatography (dichloromethane/methanol (5% to 10%))

Sources & evidence

ORD record: ord-ca3c951b079f4dca8af45c1564b6a29c
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314091B2

Reaction notes

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