Triethylamine → N-[4-(4H-Furo[2,3-e]pyrrolo[1,2-a][1,4]-diazepin-10(9H)-ylcarbonyl)phenyl]-2-methyl benzamide

HRID 1456089

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.[O:27]1[C:31]2[NH:32][CH2:33][C:34]3[N:35]([CH:37]=[CH:38][CH:39]=3)[CH2:36][C:30]=2[CH:29]=[CH:28]1>C(Cl)Cl>[O:27]1[C:31]2[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])[CH2:33][C:34]3[N:35]([CH:37]=[CH:38][CH:39]=3)[CH2:36][C:30]=2[CH:29]=[CH:28]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 1.1 mmol of 4-[(2-methylbenzoyl)amino]benzoyl chloride in 10 ml of methylene chloride, cooled to 0° C. is added 1.5 mmol of triethylamine. To the mixture is added 1 mmol of 9,10-dihydro-4H-furo[2,3-e]pyrrolo[1,2-a][1,4]diazepine and the mixture stirred at room temperature for 2 hours. The reaction mixture is concentrated in vacuo and 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 volatiles concentrated in vacuo to give a solid which is purified by flash chromatography to give the desired product.

Workup

concentrationThe reaction mixture is concentrated in vacuo
dissolutionthe residue is dissolved in 100 ml of ethyl acetate
washwashed with water, 2N citric acid, aqueous NaHCO3 and brine
dry with materialThe solution is dried with Na2SO4
concentrationthe volatiles concentrated in vacuo
customto give a solid which
customis purified by flash chromatography

Sources & evidence

ORD record: ord-d5195dadfb7d4c38a833f527c8f316fc
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05843944

Linked notes

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