6-Chloronicotinoyl Chloride → 10-[(6-Chloro-3-pyridinyl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine
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.[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][N:17]=1>ClCCl>[Cl:15][C:16]1[N:17]=[CH:18][C:19]([C:20]([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:21])=[CH:23][CH:24]=1Participants
4
Procedure
A solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (100 mmol) and N,N′-diisopropylethyl amine (130 mmol) in dichloromethane (500 mL) was cooled to 0° C. 6-Chloronicotinoyl chloride (130 mmol) was added dropwise under nitrogen. The solution was stirred for one hour as it returned to room temperature. The reaction mixture was filtered through a sica gel pad, washed with 0.5 N sodium hydroxide and water, dried over anhydrous magnesium sulfate. The solution was again filtered through a silica gel pad and evaporated to dryness in vacuo. The residual oil crystallized from diethyl ether to provide the title compound as a colorless crystalline solid, m.p. 165–167° C.
Workup
- customreturned to room temperature
- filtrationThe reaction mixture was filtered through a sica gel pad
- washwashed with 0.5 N sodium hydroxide and water
- dry with materialdried over anhydrous magnesium sulfate
- filtrationThe solution was again filtered through a silica gel pad
- customevaporated to dryness in vacuo
- customThe residual oil crystallized from diethyl ether
Sources & evidence
- ORD record
- ord-b9cc5beb650a43e8ad8b1ccc74e12cfd
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07064120B2
Reaction notes
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