Potassium Carbonate → 5-{4-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl}-1,3,4-thiadiazol-2-amine

HRID 561191Notes

Reaction equation

Cl.[F:2][C:3]([F:18])([F:17])[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[O:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.Br[C:20]1[S:24][C:23]([NH2:25])=[N:22][N:21]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:18][C:3]([F:2])([F:17])[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[O:6][CH:7]1[CH2:12][CH2:11][N:10]([C:20]2[S:24][C:23]([NH2:25])=[N:22][N:21]=2)[CH2:9][CH2:8]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-[2-(trifluoromethyl)phenoxy]piperidine hydrochloride (5.5 g, 2.2 mmol) in DMF (50 mL) was added 5-bromo-1,3,4-thiadiazol-2-amine (3.3 g, 2.2 mmol) and K2CO3 (9.1 g, 6.6 mmol). The reaction was heated at 80° C. with stirring overnight. After cooling, the salt was removed by filtration and the filtrate was evaporated in vacuo. The residue was triturated with EtOAc to afford the title compound.

Workup

temperatureAfter cooling
customthe salt was removed by filtration
customthe filtrate was evaporated in vacuo
customThe residue was triturated with EtOAc

Sources & evidence

ORD record: ord-2cb4ec98707546dbaad3ef52a0d6935d
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063224B2

Reaction notes

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