Ethyl Acetate → N-(5-(7-Chloro-3-(2-chlorobenzyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)pyridin-2-yl)acetamide

HRID 1910693Notes

Reaction equation

[Cl:1][C:2]1[CH:40]=[CH:39][C:5]2[N:6](CC3C=CC(OC)=CC=3)[C:7](=[O:29])[CH:8]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[N:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([NH:17][C:18](=[O:20])[CH3:19])=[N:15][CH:16]=3)[C:4]=2[CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].C(OCC)(=O)C>C1(OC)C=CC=CC=1>[Cl:1][C:2]1[CH:40]=[CH:39][C:5]2[NH:6][C:7](=[O:29])[CH:8]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[N:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([NH:17][C:18](=[O:20])[CH3:19])=[N:15][CH:16]=3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

N-(5-(7-Chloro-3-(2-chlorobenzyl)-1-(4-methoxybenzyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)pyridin-2-yl)acetamide (210 mg, 0.366 mmol) was dissolved in anisole (1 mL) under nitrogen and AlCl3 (195 mg, 1.465 mmol) was added in one portion. The resulting orange solution was heated to 85° C. for 2 h then allowed to cool. Ice and ethyl acetate were added and the mixture was stirred for 30 min then partitioned and the organic layer was washed with water then brine and dried (MgSO4). Chromatography on silica gel eluting with 10%-50%-70% ethyl acetate in hexanes gave the product (120 mg, 72% yield). 1H-NMR (300 MHz, CDCl3) δ 7.62-7.5 (m, 3H), 7.5-7.20 (m, 7H), 6.49 (s, 1H), 6.47 (s, 1H), 4.31 (dd, 1H), 4.25-4.17 (m, 2H), 3.59 (dd, 1H), 3.35 (dd, 1H). HRMS (ES+) m/z calcd for C23H18Cl2N4O2 [M+H]+, 453.0885. found, 453.0872.

Workup

temperatureto cool
customthen partitioned
washthe organic layer was washed with water
dry with materialbrine and dried (MgSO4)

Sources & evidence

ORD record: ord-8729b24f764c4799a5a878bae4a09fd0
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604023B2

Reaction notes

Loading…