Water → ethyl 4-methyl-2-[4-(propan-2-yloxy)-3-(1H-1,2,3,4-tetrazol-1-yl)phenyl]-1,3-thiazole-5-carboxylate

HRID 1051296Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:12]2[S:13][C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:15]([CH3:17])[N:16]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[N-:23]=[N+:24]=[N-:25].[Na+].[CH:27](OCC)(OCC)OCC.O>C(O)(=O)C.C(OCC)(=O)C>[CH3:17][C:15]1[N:16]=[C:12]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[C:2]([N:1]3[CH:27]=[N:25][N:24]=[N:23]3)[CH:3]=2)[S:13][C:14]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension was prepared by suspending 1.23 g of ethyl 2-[3-amino-4-(propan-2-yloxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate in 20 mL of acetic acid. A reaction mixture solution prepared by adding 478 mg of sodium azide and 1.09 g of triethyl ortho formate to the suspension was heated at 70° C. for 2 hours under a nitrogen atmosphere. After cooling the reaction mixture solution to room temperature, water was added to the reaction mixture solution, and extraction was performed using ethyl acetate. The organic layer was washed with saline, dried and concentrated under reduced pressure and purified by a conventional method to obtain 1.13 g of ethyl 4-methyl-2-[4-(propan-2-yloxy)-3-(1H-1,2,3,4-tetrazol-1-yl)phenyl]-1,3-thiazole-5-carboxylate.

Workup

customA suspension was prepared
customA reaction mixture solution prepared
temperatureAfter cooling the reaction mixture solution to room temperature
washThe organic layer was washed with saline
customdried
concentrationconcentrated under reduced pressure
custompurified by a conventional method

Sources & evidence

ORD record: ord-fc5e03199b2740afac0085634c177302
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388174B2

Reaction notes

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