Ammonia → 6,11-Dihydro-11-[[3-[3-(1-pyrrolidinyl)propyl]-1-piperidinyl]carbonyl]-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one

HRID 2106696Notes

Reaction equation

HRID 2106696 reaction equation
Cl[C:2]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7](=[O:15])[C:6]2[CH:16]=[CH:17][CH:18]=[N:19][C:5]1=2)=[O:3].[N:20]1([CH2:25][CH2:26][CH2:27][CH:28]2[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]2)[CH2:24][CH2:23][CH2:22][CH2:21]1.C(#N)C.N>ClCCl.C1CCCCC1.CO>[N:20]1([CH2:25][CH2:26][CH2:27][CH:28]2[CH2:33][CH2:32][CH2:31][N:30]([C:2]([N:4]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[NH:8][C:7](=[O:15])[C:6]4[CH:16]=[CH:17][CH:18]=[N:19][C:5]3=4)=[O:3])[CH2:29]2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6342AcetonitrileHCID 1420998311-(chlorocarbonyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-5-oneHCID 150573053-[3-(Pyrrolidin-1-yl)propyl]piperidine

Product 1

HCID 143696666,11-Dihydro-11-[[3-[3-(1-pyrrolidinyl)propyl]-1-piperidinyl]carbonyl]-5H-pyrido[2,3-b][1,5]benzodiazepin-5-oneYield 56%

Reagents, catalysts & solvents 1

HCID 69163855HCID 69163855, compoundSolvent

Procedure

Prepared analogously to Example 4 from 11-(chlorocarbonyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one and 3-[3-(1-pyrrolidinyl)propyl]piperidine in a yield of 56% of theory. Colourless crystals, m.p. 174°-176° C. (acetonitrile), Rf 0.65 (Macherey-Nagel, Polygram® SIL G/UV254, pre-coated plastic sheets for TLC; eluant: dichloromethane/cyclohexane/methanol/conc. ammonia 68/15/15/2, v/v/v/v)

Sources & evidence

ORD record
ord-4a912702476a4c2498a98ca1ca2edc99
Source dataset
uspto-grants-1990_06
Patent number
US04931436

Reaction notes

Loading…