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

HRID 465074

Reaction equation

HRID 465074 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].[N:21]1([CH2:26][C@@H:27]2[CH2:31][CH2:30][CH2:29][NH:28]2)[CH2:25][CH2:24][CH2:23][CH2:22]1.C(OCC)(=O)C>C(O)C>[N:21]1([CH2:26][C@@H:27]2[CH2:31][CH2:30][CH2:29][N:28]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])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 12005311-(Chloroacetyl)-5,11-dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-oneHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine

Product 1

HCID 13578576(S)-5,11-Dihydro-11-[[2-[(1-pyrrolidinyl)methyl]-1-pyrrolidinyl]acetyl]-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-[(1-pyrrolidinyl)methyl]pyrrolidine to give colorless crystals, mp. 192°-193° C. (ethyl acetate). [α]D20 =-18.1° (ethanol).

Sources & evidence

ORD record
ord-926850534af8480e9d6b71f8d154c4bc
Source dataset
uspto-grants-1985_10
Patent number
US04550107

Linked notes

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