5,11-Dihydro-11-ethyl-5-methyl-8-phenylethynyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one → 2-ethyl-9-methyl-13-[(Z)-2-phenylethenyl]-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

HRID 724941Notes

Reaction equation

HRID 724941 reaction equation
[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([C:14]#[C:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:13][C:8]=2[C:7](=[O:22])[N:6]([CH3:23])[C:5]2[CH:24]=[CH:25][CH:26]=[N:27][C:4]1=2)[CH3:2].[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C(O)C>[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12](/[CH:14]=[CH:15]\[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:13][C:8]=2[C:7](=[O:22])[N:6]([CH3:23])[C:5]2[CH:24]=[CH:25][CH:26]=[N:27][C:4]1=2)[CH3:2]

Participants

5

Reactant 2

HCID 105701215,11-Dihydro-11-ethyl-5-methyl-8-phenylethynyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 53276242-ethyl-9-methyl-13-[(Z)-2-phenylethenyl]-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-oneYield 16.5%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

5,11-Dihydro-11-ethyl-5-methyl-8-phenylethynyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.12 g, 0.34 mmol) was hydrogenated over Lindlar catalyst in ethanol under 50 p.s.i. of hydrogen. Workup and purification as described in Example 42 afforded 20 mg of the title compound as a yellow-orange oil.

Workup

  1. customWorkup and purification

Sources & evidence

ORD record
ord-4cd800553e264f778b4121e91c7bed67
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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