2-Methoxyacetohydrazide → 9-Bromo-2-methoxymethyl-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one

HRID 1786174Notes

Reaction equation

HRID 1786174 reaction equation
C([O:3][C:4](=O)[NH:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:7]=1[C:13]#[N:14])C.[CH3:16][O:17][CH2:18][C:19]([NH:21][NH2:22])=O>>[Br:12][C:9]1[CH:10]=[CH:11][C:6]2[NH:5][C:4](=[O:3])[N:22]3[N:21]=[C:19]([CH2:18][O:17][CH3:16])[N:14]=[C:13]3[C:7]=2[CH:8]=1

Participants

3

Reactant 2

HCID 27595322-MethoxyacetohydrazideHCID 18367857Ethyl (4-bromo-2-cyanophenyl)carbamate

Product 1

HCID 1363323289-Bromo-2-methoxymethyl-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-oneYield 92%

Procedure

As described for example 1a) (4-bromo-2-cyano-phenyl)-carbamic acid ethyl ester (19.9 g, 74.2 mmol) instead of (4-chloro-2-cyano-phenyl)-carbamic acid ethyl ester using methoxymethyl-carboxylic acid hydrazide instead of cyclopropane-carboxylic acid hydrazide, was converted to the title compound (21.1 g, 92%) which was obtained as a light yellow solid. MS: m/e=308.9/310.9 [M+H]+.

Sources & evidence

ORD record
ord-10b35571eb37418eb7d2de4465667b0c
Source dataset
uspto-grants-2009_03
Patent number
US07507729B2

Reaction notes

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