Water → 5-(4-Bromo-phenyl)-6-(4-chloro-phenyl)-3-(3-methanesulfonyl-phenyl)-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one

HRID 1024606Notes

Reaction equation

C(O[C:4]([C:6]1[N:7]=[N:8][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:13]=2)[C:10]=1[NH2:11])=[O:5])C.[Br:22][C:23]1[CH:38]=[CH:37][C:26]([C:27](Cl)=[N:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[CH:25][CH:24]=1.O>ClC(Cl)C.C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Br:22][C:23]1[CH:24]=[CH:25][C:26]([C:27]2[N:28]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[C:4](=[O:5])[C:6]3[N:7]=[N:8][N:9]([C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([S:18]([CH3:21])(=[O:19])=[O:20])[CH:13]=4)[C:10]=3[N:11]=2)=[CH:37][CH:38]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 5-amino-1-(3-methanesulfonyl-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester (310 mg, 1 mmol), 4-bromo-N-(4-chloro-phenyl)-benzimidoyl chloride (1.2 mmol) and TiCl4 (2 mmol) in anhydrous dichloroethane (5 mL) is heated to 150° C. for 14 h. After cooling down to room temperature, the mixture is diluted with CH2Cl2 (20 mL) and treated with water (30 mL). The solid is collected by filtration and washed with MeOH (5 ml) to provide the crude 5-(4-bromo-phenyl)-6-(4-chloro-phenyl)-3-(3-methanesulfonyl-phenyl)-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one as yellow solid which is used for next step without further purification.

Workup

temperatureAfter cooling down to room temperature
filtrationThe solid is collected by filtration
washwashed with MeOH (5 ml)

Sources & evidence

ORD record: ord-5bf6fc0e559442b3bc8000ea74818e68
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722691B2

Reaction notes

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