Cyclohexene → 3-(4-Oxo-7-styryl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-benzonitrile

HRID 859569Notes

Reaction equation

HRID 859569 reaction equation
[O:1]=[C:2]1[CH2:8][C:7]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])=[N:6][C:5]2[CH:17]=[CH:18][C:19]([C:21]#[C:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:20][C:4]=2[NH:3]1.C1CCCCC=1>>[O:1]=[C:2]1[CH2:8][C:7]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])=[N:6][C:5]2[CH:17]=[CH:18][C:19]([CH:21]=[CH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:20][C:4]=2[NH:3]1

Participants

3

Reactant 2

HCID 8079CyclohexeneHCID 98203213-(4-Oxo-7-phenylethynyl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-benzonitrile

Product 1

HCID 695929663-(4-Oxo-7-styryl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-benzonitrile

Procedure

Prepared from 3-(4-oxo-7-phenylethynyl-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl)-benzonitrile (Example 2) by catalytic hydrogenation with Lindlar-catalyst in the presence of 10 eq. cyclohexene according to the general procedure G (method a). Obtained as a light yellow solid (159 mg).

Sources & evidence

ORD record
ord-d45c77f36c314c7a9c614c62a5fb8ba3
Source dataset
uspto-grants-2006_12
Patent number
US07151098B2

Reaction notes

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