4-Bromobenzoyl chloride → 4-bromo-N-(3-cyclopentylpropyl)-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)benzamide

HRID 551938Notes

Reaction equation

[CH:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10]2[CH:11]=[CH:12][C:13]3[C:18](=[O:19])[O:17][C:16]([CH3:21])([CH3:20])[O:15][C:14]=3[CH:22]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>N1C=CC=CC=1>[Br:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([N:9]([CH2:8][CH2:7][CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:10]2[CH:11]=[CH:12][C:13]3[C:18](=[O:19])[O:17][C:16]([CH3:20])([CH3:21])[O:15][C:14]=3[CH:22]=2)=[O:29])=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a cold (0° C.) solution of 7-[(3-cyclopentylpropyl)amino]-2,2-dimethyl-4H-1,3-benzodioxin-4-one (1.70 g, 5.60 mmol) in pyridine (10 mL) was added 4-bromobenzoyl-chloride (Aldrich, 1.47 g, 6.72 mmol) and the resulting reaction mixture was stirred 10 min at 0° C., 30 min at rt and 7 hrs at 60° C. The solvent was removed under reduced pressure. Purification by flash chromatography on silicagel (EtOAc/c-Hex (15/85)) gave 1.6 g (59%) of the title compound as a white solid. HPLC, Rt: 5.2 min (purity: 99.5%). 1H NMR (CDCl3) δ: 7.81 (d, J=7.3 Hz, 1H), 7.35 (d, J=8.7 Hz, 2H), 7.18 (d, J=8.7 Hz, 2H), 6.76 (dd, J=1.9 Hz, J=8.3 Hz, 1H), 6.56 (d, J=1.9 Hz, 1H), 3.91 (t, J=7.9 Hz, 2H), 1.80-1.25 (m, 17H), 1.12-0.95 (m, 2H).

Workup

customthe resulting reaction mixture
customThe solvent was removed under reduced pressure
customPurification by flash chromatography on silicagel (EtOAc/c-Hex (15/85))

Sources & evidence

ORD record: ord-efc3c93ee3c14fe982d86684911d0be1
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947851B2

Reaction notes

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