N-Methylaniline → 5-Chloro-2-ethyl-9-methyl-13-{[methyl(phenyl)amino]methyl}-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

HRID 724984Notes

Reaction equation

HRID 724984 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[C:8]3[CH:18]=[C:17]([CH2:19]Cl)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.[CH3:23][NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[C:8]3[CH:18]=[C:17]([CH2:19][N:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH3:23])[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1

Participants

3

Reactant 2

HCID 7515N-MethylanilineHCID 108307382-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Product 1

HCID 4706745-Chloro-2-ethyl-9-methyl-13-{[methyl(phenyl)amino]methyl}-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-oneYield 41%

Procedure

The 2-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.050 g, 0.15 mmol) was dissolved in N-methylaniline (1 mL) and stirred for 3 days. The mixture was purified by column chromatography (hexanes to ethyl acetate gradient) to give the title compound (0.025 g, 41%), m.p. 55°-57° C., foam.

Workup

  1. customThe mixture was purified by column chromatography (hexanes to ethyl acetate gradient)

Sources & evidence

ORD record
ord-22c36113db334c77ac4a29e77143e8b4
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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