Triethylamine → Ethyl 10,11-Dihydro-10-[4-[(2-methylbenzoyl)amino]-benzoyl]-5H-pyrrolo[2,1-c][1,4]benzodiazepine-7-carboxylate

HRID 440045Notes

Reaction equation

HRID 440045 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:13]=[CH:14][C:8]=3[NH:7][CH2:6][C:5]=12.C(N(CC)CC)C.[CH3:27][C:28]1[CH:45]=[CH:44][CH:43]=[CH:42][C:29]=1[C:30]([NH:32][C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1)=[O:31]>C(Cl)Cl>[CH3:27][C:28]1[CH:45]=[CH:44][CH:43]=[CH:42][C:29]=1[C:30]([NH:32][C:33]1[CH:41]=[CH:40][C:36]([C:37]([N:7]2[C:8]3[CH:14]=[CH:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][C:9]=3[CH2:10][N:4]3[CH:3]=[CH:2][CH:1]=[C:5]3[CH2:6]2)=[O:38])=[CH:35][CH:34]=1)=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 107074414-[(2-methylbenzoyl)amino]benzoyl ChlorideHCID 21837067Ethyl 10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]-benzodiazepine-7-carboxylate

Product 1

HCID 21837143Ethyl 10,11-Dihydro-10-[4-[(2-methylbenzoyl)amino]-benzoyl]-5H-pyrrolo[2,1-c][1,4]benzodiazepine-7-carboxylateYield 43.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.2 g of ethyl 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-7-carboxylate in 100 ml of methylene chloride is cooled to 0° C. and 10 ml of triethylamine added followed by 1.5 g of 4-[(2-methylbenzoyl)amino)benzoyl chloride. The reaction mixture is stirred at room temperature for 18 hours and concentrated in vacuo to a residue which is partitioned between water and chloroform. The organic layer is dried over Na2SO4 and concentrated in vacuo to a residue. The residue is purified by column chromatography on silica gel by elution with 40% ethyl acetate-hexane to give 1.0 g of the desired product as a solid; mass spectrum (M+H)494.

Workup

  1. concentrationconcentrated in vacuo to a residue which
  2. customis partitioned between water and chloroform
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated in vacuo to a residue
  5. customThe residue is purified by column chromatography on silica gel by elution with 40% ethyl acetate-hexane

Sources & evidence

ORD record
ord-6e04c3bdd7414f368f79f2f294a9a32a
Source dataset
uspto-grants-1996_05
Patent number
US05516774

Reaction notes

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