Ethyl 5-amino-1-phenyl-1H-1,2,3-triazole-4-carboxylate → HCID 57897877, compound

HRID 1693568Notes

Reaction equation

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

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 5-amino-1-phenyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester (30 mg, 0.33 mmol), 4-bromo-N-(4-chloro-phenyl)-benzimidoyl chloride (51 mg, 0.16 mmol) and TiCl4 (20 μL) in anhydrous dichloroethane (1 mL) is heated in microwave reactor at 170° C. for 1 h and then at 115° C. for 48 h in an oil bath. After cooling down to room temperature, the mixture is worked up as in example 2 and purified by flash column chromatography (silica gel, 0˜30% EtOAc/hexane) to provide the title compound 5-(4-Bromo-phenyl)-6-(4-chloro-phenyl)-3-phenyl-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one as white solid. (45 mg, 73%). 1H NMR (CDCl3) δ (ppm) 8.15(d, 2H), 7.59(t, 2H), 7.49(t, 1H), 7.43 (d, 2H), 7.37(d, 2H), 7.21(d, 2H), 7.10(d, 2H), 2.87(m, 1H). HPLC-MS calculated C22H13BrClN5O (M+1+): 478.0. Found: 478.0.

Workup

temperatureAfter cooling down to room temperature
custompurified by flash column chromatography (silica gel, 0˜30% EtOAc/hexane)

Sources & evidence

ORD record: ord-0df520ed76834532900c15da1ef31cbe
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158634B2

Reaction notes

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