Dichloromethane → 10-[(4-Chloro-2-methylphenoxy)acetyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([O:9][CH2:10][C:11](Cl)=[O:12])[CH:3]=1.[CH:14]1[CH:15]=[CH:16][N:17]2[CH2:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[NH:20][CH2:19][C:18]=12.C(N(CC)CC)C.[Cl:35]CCl>>[Cl:35][C:7]1[CH:2]=[CH:3][C:4]([O:9][CH2:10][C:11]([N:20]2[C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[CH2:23][N:17]3[CH:16]=[CH:15][CH:14]=[C:18]3[CH2:19]2)=[O:12])=[C:5]([CH3:8])[CH:6]=1Participants
5
Procedure
To a solution of 4-chloro-o-tolyloxyacetic acid chloride of step A (17.4 mmol) in dichloromethane (25 mL) was added a solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (17.4 mmol) and triethylamine (19.14 mmol) in dichloromethane (25 mL) in a rapid dropwise fashion. The mixture was stirred for one hour at room temperature. The reaction mixture was washed with 0.1 N hydrochloric acid (2×) and water (1×), dried over anhydrous sodium sulfate and evaporated. The product was isolated by crystallization from hot ethyl acetate/t-butyl methyl ether (2/1), m.p. 166-167° C. MS [(+)ESI, m/z]: 367 [M+H]+ Anal. Calcd for C21H19CIN2O2: C, 68.76; H, 5.22; N, 7.64. Found: C, 68.53; H, 5.18; N, 7.53.
Workup
- washThe reaction mixture was washed with 0.1 N hydrochloric acid (2×) and water (1×)
- dry with materialdried over anhydrous sodium sulfate
- customevaporated
- customThe product was isolated by crystallization from hot ethyl acetate/t-butyl methyl ether (2/1), m.p. 166-167° C
Sources & evidence
- ORD record
- ord-2c2374e554f5433cb239699ed4a633d3
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691848B2
Reaction notes
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