Benzylamine → HCID 68690301, compound

HRID 2244286Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[C:21]([C:24]([NH:26][CH2:27][C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)=[O:25])=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[CH2:34]([NH2:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>ClCCl>[CH2:34]([NH:41][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[C:21]([C:24]([NH:26][CH2:27][C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)=[O:25])=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])=[CH:4][CH:3]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 10-[(6-chloropyridin-3-yl)carbonyl]-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 117 (0.100 g, 0.219 mmol) and benzylamine (0.12 mL, 1.094 mmol) was heated to 100° C. in a sealed tube for 17 hours. The cooled reaction mixture was then diluted with dichloromethane (10 mL), washed with saturated aqueous sodium bicarbonate solution (10 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford a yellow semi-solid. Purification by flash chromatography using a solvent gradient of 1 to 5% methanol in dichloromethane gave a white solid that was triturated with diethyl ether to afford the title compound (0.054 g, 47%) as a white solid.

Workup

customThe cooled reaction mixture
washwashed with saturated aqueous sodium bicarbonate solution (10 mL)
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customto afford a yellow semi-solid
customPurification by flash chromatography
customgave a white solid
customthat was triturated with diethyl ether

Sources & evidence

ORD record: ord-5f9e5d2070c84bc082480fd3255d146b
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678787B2

Reaction notes

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