Hydrochloric Acid → HCID 67282441, compound

HRID 1910703Notes

Reaction equation

[Cl:1][C:2]1[CH:43]=[CH:42][C:5]2[N:6](CC3C=CC(OC)=CC=3)[C:7](=[O:32])[CH:8]([CH2:21][C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=3)[N:9]=[C:10]([N:11]3[CH2:20][CH2:19][C:14]4(OCC[O:15]4)[CH2:13][CH2:12]3)[C:4]=2[CH:3]=1.Cl>O1CCOCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:43]=[CH:42][C:5]2[NH:6][C:7](=[O:32])[CH:8]([CH2:21][C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=3)[N:9]=[C:10]([N:11]3[CH2:12][CH2:13][C:14](=[O:15])[CH2:19][CH2:20]3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

7-Chloro-1-(4-methoxybenzyl)-3-(naphthalen-2-ylmethyl)-5-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-1H-benzo[e][1,4]diazepin-2(3H)-one (0.14 g, 0.24 mmol) was dissolved in 1,4-dioxane (4 mL), and concentrated aqueous hydrochloric acid (4 mL) was added. The reaction mixture was stirred at 60° C. for 5 hours, then the temperature increased to 80° C. for 2 hours. The solution was cooled, diluted with ethyl acetate, washed with saturated sodium bicarbonate solution, brine, dried with sodium sulfate, decanted and concentrated in the presence of silica. Chromatography provided 7-chloro-3-(naphthalen-2-ylmethyl)-5-(4-oxopiperidin-1-yl)-1H-benzo[e][1,4]diazepin-2(3H)-one (22 mg, 22% yield). ESI m/z measured 432.1487 [M+H]+. calculated 432.1479.

Workup

temperaturethe temperature increased to 80° C. for 2 hours
temperatureThe solution was cooled
washwashed with saturated sodium bicarbonate solution, brine
dry with materialdried with sodium sulfate
customdecanted
concentrationconcentrated in the presence of silica

Sources & evidence

ORD record: ord-edf99ef26bf4423593770d967f8a6a56
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604023B2

Reaction notes

Loading…