Formaldehyde → 11-[4-[(Cyclohexyl)methylamino]-but-2-ynyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 1084703Notes

Reaction equation

HRID 1084703 reaction equation
[CH2:1]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:15])[NH:7][C:6]2[CH:16]=[CH:17][CH:18]=[N:19][C:5]1=2)[C:2]#[CH:3].[CH2:20]=O.[CH:22]1([CH2:28][NH2:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH:22]1([CH2:28][NH:29][CH2:20][C:3]#[C:2][CH2:1][N:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8](=[O:15])[NH:7][C:6]3[CH:16]=[CH:17][CH:18]=[N:19][C:5]2=3)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 76688CyclohexanemethylamineHCID 145520855,11-dihydro-11-(2-propynyl)-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Product 1

HCID 2006247111-[4-[(Cyclohexyl)methylamino]-but-2-ynyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneYield 17%

Procedure

Prepared analogously to Example (1b) from 5,11-dihydro-11-(prop-2-ynyl)-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, paraformaldehyde and (cyclohexyl)methylamine in a yield of 17% of theory. Colourless crystals m.p. 133°-134° C. (diethyl ether).

Sources & evidence

ORD record
ord-47ab0f710ea8479eb3f2fe1a6e0f199d
Source dataset
uspto-grants-1991_04
Patent number
US05006522

Reaction notes

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