11-(Chloroacetyl)-5,11-dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-one → (S)-5,11-Dihydro-11-[[2-[(4-methyl-1-piperazinyl)methyl]-1-pyrrolidinyl]-acetyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 465079Notes

Reaction equation

HRID 465079 reaction equation
Cl[CH2:2][C:3]([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].[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([CH2:28][C@@H:29]2[CH2:33][CH2:32][CH2:31][NH:30]2)[CH2:24][CH2:23]1>>[CH3:21][N:22]1[CH2:23][CH2:24][N:25]([CH2:28][C@@H:29]2[CH2:33][CH2:32][CH2:31][N:30]2[CH2:2][C:3]([N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[C:9](=[O:16])[NH:8][C:7]3[CH:17]=[CH:18][CH:19]=[N:20][C:6]2=3)=[O:4])[CH2:26][CH2:27]1

Participants

3

Reactant 2

HCID 12005311-(Chloroacetyl)-5,11-dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-oneHCID 132751161-Methyl-4-[(2S)-pyrrolidin-2-ylmethyl]piperazine

Product 1

HCID 13578578(S)-5,11-Dihydro-11-[[2-[(4-methyl-1-piperazinyl)methyl]-1-pyrrolidinyl]-acetyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Procedure

The title compound is prepared analogously to Example 31 from 11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and (S)-(+)-2-[(4-methyl-1-piperazinyl) methyl]pyrrolidine to give colorless crystals, mp. 182°-185° C. (D) (from ethyl acetate/methanol 99:1 v/v); [α]D20 =-11.2° (ethanol).

Sources & evidence

ORD record
ord-dbe8ec8059e341dabe8dae53be5dfcaf
Source dataset
uspto-grants-1985_10
Patent number
US04550107

Reaction notes

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