Water → 10-[(6-Chloro-3-pyridinyl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

HRID 440759Notes

Reaction equation

HRID 440759 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[NH:7][CH2:6][C:5]=12.C(N(CC)CC)C.[Cl:22][C:23]1[N:28]=[CH:27][C:26]([C:29](Cl)=[O:30])=[CH:25][CH:24]=1.O>C(Cl)Cl>[Cl:22][C:23]1[N:28]=[CH:27][C:26]([C:29]([N:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][N:4]3[CH:3]=[CH:2][CH:1]=[C:5]3[CH2:6]2)=[O:30])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27821656-Chloronicotinoyl ChlorideHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 2194772510-[(6-Chloro-3-pyridinyl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepineYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.0 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 50 ml of dry methylene chloride, under nitrogen, and 7.0 ml of triethylamine is added 1.43 g of 6-chloro-pyridine-3-carbonyl chloride. The reaction mixture is stirred at room temperature for 16 hours and poured into 100 ml of water. The organic layer is separated, washed with 2% HCl, water, saturated NaHCO3, and dried (Na2SO4). The solvent is evaporated An vacuo to give a residue which is columned on silica gel by elution with 7:1 to 1:1 ethyl acetate:hexane to give 1.76 g of the desired product as a yellowish crystalline solid. M+H=324.

Workup

  1. customThe organic layer is separated
  2. washwashed with 2% HCl, water, saturated NaHCO3
  3. dry with materialdried (Na2SO4)
  4. customThe solvent is evaporated An vacuo
  5. customto give a residue which
  6. washis columned on silica gel by elution with 7:1 to 1:1 ethyl acetate

Sources & evidence

ORD record
ord-a2aa1912f5a94012897a5d83e0fbdabd
Source dataset
uspto-grants-1996_05
Patent number
US05521173

Reaction notes

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