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

HRID 465073Notes

Reaction equation

HRID 465073 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].[CH2:21]([N:23]([CH2:26][C@@H:27]1[CH2:31][CH2:30][CH2:29][NH:28]1)[CH2:24][CH3:25])[CH3:22].C(OCC)(=O)C.CO>C(O)C>[CH2:21]([N:23]([CH2:26][C@@H:27]1[CH2:31][CH2:30][CH2:29][N:28]1[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])[CH2:24][CH3:25])[CH3:22]

Participants

5

Reactant 3

HCID 12005311-(Chloroacetyl)-5,11-dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-oneHCID 7141622(S)-N-Ethyl-N-(pyrrolidin-2-ylmethyl)ethanamineHCID 21584119Ethylacetate methanol

Product 1

HCID 13578573(S)-11-[[2-[(Diethylamino)methyl]-1-pyrrolidinyl]-acetyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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-[(diethylamino)methyl]pyrrolidine to give colorless crystals, mp. 192°-193° C. (ethyl acetate/methanol 99:1 v/v); [α]D20 =29.4° (ethanol).

Sources & evidence

ORD record
ord-3a4062283f4c495f9d8e3ae4dff28bd9
Source dataset
uspto-grants-1985_10
Patent number
US04550107

Reaction notes

Loading…