2-Amino-4-chlorophenol → 2,2-dimethyl-6-[8-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamino]-4H-benzo[1,4]oxazin-3-one

HRID 2273017Notes

Reaction equation

HRID 2273017 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:8]3[N:9]([N:13]=[C:14]([NH2:16])[N:15]=3)[CH:10]=[CH:11][N:12]=2)[CH:4]=[N:3]1.Cl[C:18]1[CH:19]=[CH:20][C:21]2[O:26][C:25]([CH3:28])([CH3:27])[C:24](=[O:29])[NH:23][C:22]=2[CH:30]=1.NC1C=C(Cl)C=CC=1O.BrC(C)(C)C(Br)=O>>[CH3:27][C:25]1([CH3:28])[C:24](=[O:29])[NH:23][C:22]2[CH:30]=[C:18]([NH:16][C:14]3[N:15]=[C:8]4[C:7]([C:5]5[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=5)=[N:12][CH:11]=[CH:10][N:9]4[N:13]=3)[CH:19]=[CH:20][C:21]=2[O:26]1

Participants

5

Reactant 4

HCID 72652-Amino-4-chlorophenolHCID 886852-Bromo-2-methylpropionyl bromideHCID 105604586-Chloro-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-oneHCID 665833238-(1-Methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine

Product 1

HCID 897760032,2-dimethyl-6-[8-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamino]-4H-benzo[1,4]oxazin-3-one

Procedure

8-(1-Methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine is coupled with 6-chloro-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one, available by reaction of 2-amino-4-chlorphenol with 2-bromo-2-methyl-propanoyl bromide under basic conditions, using general procedure 2 gave the title compound as a solid.

Sources & evidence

ORD record
ord-22d96d872fa9480d9c77dd57330278ff
Source dataset
uspto-grants-2015_09
Patent number
US09120804B2

Reaction notes

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