4-(2-Chloroethyl)benzoic acid → 5,10,11,11a-tetrahydro-9-[2-(4-carboxyphenyl)-ethoxy]-11-methoxy-8-methyl-5-oxo-1H-pyrrolo-[2,1-C][1,4]benzodiazepine-2-acrylamide
Reaction equation
[OH:1][C:2]1[C:12]2[NH:11][CH:10]([O:13][CH3:14])[CH:9]3[CH2:15][CH:16]=[CH:17][N:8]3[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:19].[C:20]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30]Cl)=[CH:25][CH:24]=1)([OH:22])=[O:21]>N1C=CC=CC=1>[C:20]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][O:1][C:2]2[C:12]3[NH:11][CH:10]([O:13][CH3:14])[CH:9]4[CH2:15][C:16]([CH:15]=[CH:9][C:10]([NH2:11])=[O:13])=[CH:17][N:8]4[C:7](=[O:18])[C:6]=3[CH:5]=[CH:4][C:3]=2[CH3:19])=[CH:25][CH:24]=1)([OH:22])=[O:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In 120 ml of pyridine were reacted 300 mg of 5,10,11,11a-tetrahydro-9-hydroxy-11-methoxy-8-methyl-5-oxo-1H-pyrrolo-[2,1-C][1,4]benzodiazepine and 1 g of 1-(4-carboxyphenyl)-2-chloroethane, for 12 hr at 50° C. After completion of the reaction, purification and recrystallization were conducted in the same manner as in Example 14 to obtain a light yellow crystal of 5,10,11,11a-tetrahydro-9-[2-(4-carboxyphenyl)-ethoxy]-11-methoxy-8-methyl-5-oxo-1H-pyrrolo-[2,1-C][1,4]benzodiazepine-2-acrylamide having a melting point of 193° to 195° C. Further, this product was converted to a corresponding sodium salt in the same manner as in Example 14. The yield of the sodium salt was 350 mg.
Workup
- customAfter completion of the reaction, purification and recrystallization
Sources & evidence
- ORD record
- ord-56f08a1ef6fd495c87b48f0cc5f2e6d7
- Source dataset
- uspto-grants-1986_05
- Patent number
- US04587052
Reaction notes
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