Potassium Carbonate → HCID 67125226, compound

HRID 874188Notes

Reaction equation

Br[CH2:2][C:3]1[S:4][C:5]([C:15]([O:17][CH3:18])=[O:16])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[N:7]=1.[Na].[F:20][C:21]([C:24]1[NH:28][N:27]=[N:26][N:25]=1)([F:23])[F:22].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:6]1[N:7]=[C:3]([CH2:2][N:26]2[N:27]=[N:28][C:24]([C:21]([F:23])([F:22])[F:20])=[N:25]2)[S:4][C:5]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

Conditions

Temperature: 60 °C

Procedure

5.00 g (14.4 mmol) of methyl 2-(bromomethyl)-4-(2-chlorophenyl)-1,3-thiazole-5-carboxylate were added to a solution of 10.00 g (18.7 mmol) of trifluoromethyltetrazole sodium salt in 100 ml of acetonitrile. Then 600 mg (4.32 mmol) of potassium carbonate were added to the reaction solution, and the mixture was stirred at 60° C. for 6 hours. After cooling to room temperature, the reaction solution was filtered and the mother liquor was freed from the solvent under reduced pressure. 10 ml of water were added to the residue and the mixture was extracted with ethyl acetate (3×20 ml). The combined organic phases were dried over sodium sulphate. The solvent was removed under reduced pressure and the residue was purified by chromatography. (logP: 3.60; MH+: 404; 1H-NMR (400 MHz, DMSO, ppm): 3.71 (s, 3H), 6.70 (s, 2H), 7.40-7.60 (m, 4H).

Workup

temperatureAfter cooling to room temperature
filtrationthe reaction solution was filtered
addition10 ml of water were added to the residue
extractionthe mixture was extracted with ethyl acetate (3×20 ml)
dry with materialThe combined organic phases were dried over sodium sulphate
customThe solvent was removed under reduced pressure
customthe residue was purified by chromatography

Sources & evidence

ORD record: ord-512e044beb4d4a97920d115f8727d1ea
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980886B2

Reaction notes

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