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

HRID 1598260Notes

Reaction equation

HRID 1598260 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(Cl)Cl.[CH3:23][C:24]1[CH:41]=[CH:40][CH:39]=[CH:38][C:25]=1[C:26]([NH:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)=[O:27]>C(N(CC)CC)C>[CH3:23][C:24]1[CH:41]=[CH:40][CH:39]=[CH:38][C:25]=1[C:26]([NH:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([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:34])=[CH:31][CH:30]=1)=[O:27]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 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 8471TriethylamineSolvent

Procedure

A solution of 1.2 g of ethyl 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-7-carboxylate in 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 acetatehexane 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 acetatehexane

Sources & evidence

ORD record
ord-b1ace49b277c4713af6e53df67a6ff05
Source dataset
uspto-grants-1998_04
Patent number
US05736540

Reaction notes

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