Ammonia → {6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-3-methyl-1,2-benzothiazol-5-yl}methanol

HRID 245446Notes

Reaction equation

C([SiH2][O:6][C:7](C1C=CC=CC=1)(C1C=CC=CC=1)[C:8]1[C:9]([N:19]2[CH2:24][C@H:23]([CH3:25])[O:22][C@H:21]([CH3:26])[CH2:20]2)=[C:10]([F:18])C(F)=[C:12]([C:14](=O)[CH3:15])[CH:13]=1)(C)(C)C.[S].[I-].[K+].[NH3:42].C[S:44]([CH3:46])=O>O>[CH3:26][C@H:21]1[O:22][C@@H:23]([CH3:25])[CH2:24][N:19]([C:9]2[C:8]([CH2:7][OH:6])=[CH:13][C:12]3[C:14]([CH3:15])=[N:42][S:44][C:46]=3[C:10]=2[F:18])[CH2:20]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-[5-(tert-Butyldiphenylsilanyloxymethyl)-4-[(2R,6S)-2,6-dimethyl-morpholin-4-yl]-2,3-difluorophenyl]ethanone (Intermediate 9, 0.5 g, 0.92 mmol), sulfur powder (0.06 g, 1.8 mmol), potassium iodide (0.08 g, 0.4 mmol) and 25% aqueous ammonia solution (10 mL) in DMSO (10 mL) was heated in a sealed tube at 100° C. for 4 hours. The reaction mixture was cooled and water was added. The mixture was extracted with ethyl acetate, which was dried (Na2SO4) and concentrated. The residue was purified by column chromatography (1:9 ethyl acetate:hexanes) to afford product as a yellow solid. Yield: 0.18 g (63%).

Workup

temperatureThe reaction mixture was cooled
extractionThe mixture was extracted with ethyl acetate, which
dry with materialwas dried (Na2SO4)
concentrationconcentrated
customThe residue was purified by column chromatography (1:9 ethyl acetate:hexanes)
customto afford product as a yellow solid

Sources & evidence

ORD record: ord-1aa3d375a4ca4e389ed3a671e78681b3
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658641B2

Reaction notes

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