Acetonitrile → 11-(6-chlorocaproyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Reaction equation
[C:1]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[NH:8][C:7]2[CH:17]=[CH:18][CH:19]=[N:20][C:6]1=2)(=[O:4])[CH:2]=[CH2:3].C(#N)C.C(N(CC)CC)C.[Cl:31][CH2:32][CH2:33][C:34](N1C2C=CC=CC=2C(=O)NC2C=CC=NC1=2)=O>O1CCOCC1>[Cl:31][CH2:32][CH2:33][CH2:34][CH2:3][CH2:2][C:1]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[NH:8][C:7]2[CH:17]=[CH:18][CH:19]=[N:20][C:6]1=2)=[O:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
From the thus obtained 11-haloacyl-5,11-dihydro-6H-pyrido-[2,3-b][1,4]benzodiazepin-6-ones one can easily, as described above, obtain the intermediates having in 11-position an alkenylacyl group, which can subsequently be reacted with an amine of the formula III. Thus, for example, from 11-(3-chloropropionyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one in dioxane as solvent, 11-(acryloyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepine-6-one, M.p.: 235° C. (decomp.) (from acetonitrile), was obtained with high yield after 1 hour of refluxing in the presence of an excess of triethylamine (see German Pat. No. 1,936,670).
Workup
- customobtain the intermediates
- customwith high yield after 1 hour
Sources & evidence
- ORD record
- ord-22f4996eb121403ab6784f1da04b1eaf
- Source dataset
- uspto-grants-1980_07
- Patent number
- US04210648
Reaction notes
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