(Bis(2-methoxyethyl)amino)sulfur trifluoride → N-((5-fluoro-1-(2-methyl-4-phenylthiazole-5-carbonyl)piperidin-2-yl)methyl)quinoline-8-carboxamide

HRID 60817

Reaction equation

O[CH:2]1[CH2:7][N:6]([C:8]([C:10]2[S:14][C:13]([CH3:15])=[N:12][C:11]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:9])[CH:5]([CH2:22][NH:23][C:24]([C:26]2[CH:27]=[CH:28][CH:29]=[C:30]3[C:35]=2[N:34]=[CH:33][CH:32]=[CH:31]3)=[O:25])[CH2:4][CH2:3]1.COCCN(S(F)(F)[F:46])CCOC>C(Cl)Cl>[F:46][CH:2]1[CH2:7][N:6]([C:8]([C:10]2[S:14][C:13]([CH3:15])=[N:12][C:11]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:9])[CH:5]([CH2:22][NH:23][C:24]([C:26]2[CH:27]=[CH:28][CH:29]=[C:30]3[C:35]=2[N:34]=[CH:33][CH:32]=[CH:31]3)=[O:25])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of N-((5-hydroxy-1-(2-methyl-4-phenylthiazole-5-carbonyl)piperidin-2-yl)methyl)quinoline-8-carboxamide (0.07 mmol, 0.036 g) in DCM (0.3 mL) was added to a mixture of bis(2-methoxyethyl)aminosulfur trifluoride (0.14 mmol, 0.027 mL) in DCM (0.2 mL) at −78° C. under argon. The resulting mixture was stirred at −78° C. for 1 h and at rt for another 1.5 h. The desired product was purified by preparative TLC to give N-((5-fluoro-1-(2-methyl-4-phenylthiazole-5-carbonyl)piperidin-2-yl)methyl)quinoline-8-carboxamide with unidentified stereochemistry (Y: 16%). MS (ESI) 489 (M+H).

Workup

customThe desired product was purified by preparative TLC

Sources & evidence

ORD record: ord-5080850ddb214b1684fe9feaad436637
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440982B2

Linked notes

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