Sodium hydride → 5-Chloro-2-ethyl-9-methyl-13-{[(2-methylpyridin-4-yl)oxy]methyl}-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

HRID 724970Notes

Reaction equation

HRID 724970 reaction equation
[H-].[K+].[H-].[Na+].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH3:26])[C:11](=[O:25])[C:12]3[CH:22]=[C:21]([CH2:23][OH:24])[CH:20]=[N:19][C:13]=3[N:14]([CH2:17][CH3:18])[C:15]=2[N:16]=1.[N+]([C:30]1[CH:35]=[CH:34][N:33]=[C:32]([CH3:36])[CH:31]=1)([O-])=O>>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH3:26])[C:11](=[O:25])[C:12]3[CH:22]=[C:21]([CH2:23][O:24][C:30]4[CH:35]=[CH:34][N:33]=[C:32]([CH3:36])[CH:31]=4)[CH:20]=[N:19][C:13]=3[N:14]([CH2:17][CH3:18])[C:15]=2[N:16]=1

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 82127Potassium hydrideHCID 98849Pyridine, 2-methyl-4-nitro-HCID 10615550HCID 10615550, compound

Product 1

HCID 4706975-Chloro-2-ethyl-9-methyl-13-{[(2-methylpyridin-4-yl)oxy]methyl}-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-oneYield 69%

Procedure

Using a procedure analogous to that described in Example 91, except potassium hydride was employed as the base instead of sodium hydride, the title compound, m.p. 163°-164° C., was prepared from 2-chloro-5,11-dihydro-11-ethyl-8-hydroxymethyl-5-methyl-6H-dipyrido-[3,2-b:2',3'-e][1,4]diazepin-6-one and 4-nitro-2-picoline. The yield was 69% of theory.

Sources & evidence

ORD record
ord-c682b2ea70aa42f48f17bab1ddf91c0f
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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