Triethylamine → N-[4-[(6,7-Dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepin-5-yl)carbonyl)phenyl]-2-methylbenzamide

HRID 1459530Notes

Reaction equation

[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1)=[O:5].C(N(CC)CC)C.[CH:27]1[C:37]2[N:36]3[CH:38]=[CH:39][CH:40]=[C:35]3[CH2:34][CH2:33][NH:32][C:31]=2[CH:30]=[CH:29][CH:28]=1>C(Cl)Cl.C(OCC)(=O)C>[CH:27]1[C:37]2[N:36]3[CH:38]=[CH:39][CH:40]=[C:35]3[CH2:34][CH2:33][N:32]([C:11]([C:10]3[CH:14]=[CH:15][C:7]([NH:6][C:4](=[O:5])[C:3]4[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=4[CH3:1])=[CH:8][CH:9]=3)=[O:12])[C:31]=2[CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 1.37 g (5 mmol) of 4-[(2-methylbenzoyl)amino]benzoyl chloride in 10 ml of methylene chloride, cooled to 0° C. is added 7 mmol of triethylamine and 5 mmol of 6,7-dihydro-5H-pyrrolo-[1,2-a][1,5]benzodiazepine. The cooling bath is removed and the reaction mixture is allowed to stir at room temperature for 48 hours. The volatiles are removed in vacuo to give a residue. The residue is dissolved in 100 ml of ethyl acetate and washed with water, 2N citric acid, aqueous NaHCO3 and brine. The solution is dried with Na2SO4 and the solvent removed in vacuo to give a solid. The solid is triturated with ether-hexane to give the desired product, mass spectrum (CI):422(M+H).

Workup

customThe cooling bath is removed
customThe volatiles are removed in vacuo
customto give a residue
washwashed with water, 2N citric acid, aqueous NaHCO3 and brine
dry with materialThe solution is dried with Na2SO4
customthe solvent removed in vacuo
customto give a solid
customThe solid is triturated with ether-hexane

Sources & evidence

ORD record: ord-434f2697b2ec4ca59d519ac207194933
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05854237

Reaction notes

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