Chlorine → (RS)-1-[2-(3-Chloro-furo[3,2-b]pyridin-2-ylmethyl)-piperidin-1-yl]-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanone

HRID 598605Notes

Reaction equation

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

Participants

Conditions

Temperature: -12 °C

Procedure

A solution of chlorine (28 mg) in dichloromethane (3 ml) was added to a cooled (−12° C.) solution (RS)-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-1-(2-furo[3,2-b]-pyridin-2-ylmethyl-piperidin-1-yl)methanone, E79 (170 mg) in dichloromethane (4 ml). After stirring at −12° C. for 0.5 h the reaction mixture was stirred at room temperature for 16 h then the solution was washed with saturated aqueous NaHCO3, dried (Na2SO4) and the solvent removed in vacuo. Chromatography (silica gel, 0-100% ethyl acetate-hexane then 0-10% methanol-ethyl acetate) afforded the title compound (24 mg).

Workup

stirringwas stirred at room temperature for 16 h
washthe solution was washed with saturated aqueous NaHCO3
dry with materialdried (Na2SO4)
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-032c85d7bcf4485397b4ce8810f59ad1
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897618B2

Reaction notes

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