9-Chloro-11-(chlorocarbonyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one → 9-Chloro-5,11-dihydro-11-[[3-[2-(1-pyrrolidinyl)ethyl]-1-piperidinyl]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 2106689Notes

Reaction equation

HRID 2106689 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6](=[O:18])[NH:7][C:8]3[CH:17]=[CH:16][CH:15]=[N:14][C:9]=3[N:10]([C:11](Cl)=[O:12])[C:4]=2[CH:3]=1.[N:21]1([CH2:26][CH2:27][CH:28]2[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]2)[CH2:25][CH2:24][CH2:23][CH2:22]1>ClCCl.CO>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6](=[O:18])[NH:7][C:8]3[CH:17]=[CH:16][CH:15]=[N:14][C:9]=3[N:10]([C:11]([N:30]3[CH2:31][CH2:32][CH2:33][CH:28]([CH2:27][CH2:26][N:21]4[CH2:22][CH2:23][CH2:24][CH2:25]4)[CH2:29]3)=[O:12])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 142099769-Chloro-11-(chlorocarbonyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneHCID 150573123-(2-(Pyrrolidin-1-yl)ethyl)piperidine

Product 1

HCID 143696619-Chloro-5,11-dihydro-11-[[3-[2-(1-pyrrolidinyl)ethyl]-1-piperidinyl]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneYield 42%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent2×

Procedure

Prepared analogously to Example 1 from 9-chloro-11-(chlorocarbonyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]-benzodiazepin-6-one and 3-[2-(1-pyrrolidinyl)ethyl]piperidine in a yield of 42% of theory. Colourless crystals, m.p. 136°-139° C., Rf 0.25 (Merck DC ready made TLC plates, silica gel 60 F254 ; eluant: dichloromethane/methanol/conc. ammonia 90/10/1, v/v/v).

Sources & evidence

ORD record
ord-1a8e5de03b9641dba30fb47a146ac749
Source dataset
uspto-grants-1990_06
Patent number
US04931436

Reaction notes

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