Trifluoroacetic acid → HCID 71257283, compound

HRID 710180Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[S:13][C:14]2[CH:20]=[CH:19][C:18](C3CCN(C(OC(C)(C)C)=O)CC3)=[CH:17][C:15]=2[N:16]=1.F[C:35](F)(F)[C:36](O)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[C:12]1[S:13][C:14]2[CH:20]=[C:19]([CH:36]3[CH2:35][CH2:15][NH:16][CH2:12][CH2:3]3)[CH:18]=[CH:17][C:15]=2[N:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Tert-butyl 4-{2-[2-fluoro-4-(methylsulfonyl)phenyl]benzo[d]thiazol-5-yl}piperidine-1-carboxylate (190 mg, 0.38 mmol) dissolved in DCM, cooled to 0° C., trifluoroacetic acid (0.8 ml) was added and stirred the reaction mixture at rt for 3 h. DCM and trifluoroacetic acid was removed on rotavapour to obtain the crude. Crude was washed with petether to obtain 2-[2-fluoro-4-(methylsulfonyl)phenyl]-6-(piperidin-4-yl)benzo[d]thiazole (190 mg) as an off-white solid. 2-[2-fluoro-4-(methylsulfonyl)phenyl]-6-(piperidin-4-yl)benzo[d]thiazole (190 mg, 0.38 mmol) dissolved in DCM (20 ml). To this mixture added TEA (0.3 g, 3 mmol) and stirred the reaction mixture at rt for 30 mins. Reaction mixture cooled to 0° C. and added isopropylchloro formate (92 mg, 0.75 mmol). This mixture was stirred at rt for 30 mins. Work up (DCM/H2O) followed by evaporation of the DCM on rotavapour afforded crude. Crude was triturated with diethyl ether and dried on high vacuum to afford the titled compound (60 mg) as a white solid. M.P.: 163-166° C. 1H-NMR (δ ppm, CDCl3, 400 MHz):

Workup

customDCM and trifluoroacetic acid was removed on rotavapour
customto obtain the crude
washCrude was washed with petether

Sources & evidence

ORD record: ord-e7b0501c9b264e85ac5fe4cf46875cba
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181214B2

Reaction notes

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