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

HRID 724972Notes

Reaction equation

HRID 724972 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].CC(C)([O-])C.[K+].[Cl:17][C:18]1[CH:19]=[CH:20][C:21]2[N:22]([CH3:38])[C:23](=[O:37])[C:24]3[CH:34]=[C:33]([CH2:35]Cl)[CH:32]=[N:31][C:25]=3[N:26]([CH2:29][CH3:30])[C:27]=2[N:28]=1.[C:39]1([OH:45])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]2[N:22]([CH3:38])[C:23](=[O:37])[C:24]3[CH:34]=[C:33]([CH2:35][O:45][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[CH:32]=[N:31][C:25]=3[N:26]([CH2:29][CH3:30])[C:27]=2[N:28]=1

Participants

5

Reactant 4

HCID 996PhenolHCID 2724254Sodium bis(trimethylsilyl)amideHCID 108307382-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 4706715-Chloro-2-ethyl-9-methyl-13-(phenoxymethyl)-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-oneYield 78%

Procedure

Using a procedure analogous to that described in Example 98, except sodium bis(trimethylsilyl)amide was employed as the base instead of potassium tert-butoxide, the title compound, m.p. 140°-141° C., was prepared from 2-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one and phenol. The yield was 78% of theory.

Sources & evidence

ORD record
ord-5b79f10c2a4a41f688f76e16a9a5dac3
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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