Dimethyl Sulfoxide → HCID 68584830, compound

HRID 17326Notes

Reaction equation

C(N(CC)CC)C.[CH2:8]([O:15][C:16]([NH:18][C@H:19]1[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CS(C)=O.[C:29]([C:33]1[O:34][C:35]2[C:36](=[C:38]([C:50]#[N:51])[C:39]([CH3:49])=[C:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:41]=2F)[N:37]=1)([CH3:32])([CH3:31])[CH3:30]>C(OCC)(=O)C>[CH2:8]([O:15][C:16]([NH:18][C@H:19]1[CH2:24][CH2:23][CH2:22][N:21]([C:41]2[C:40]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)=[C:39]([CH3:49])[C:38]([C:50]#[N:51])=[C:36]3[C:35]=2[O:34][C:33]([C:29]([CH3:32])([CH3:30])[CH3:31])=[N:37]3)[CH2:20]1)=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Triethylamine (83 μl, 598 μmol) and (3S)-3-benzyloxycarbonylaminopiperidine (70 mg, 298 μmol) were added to a dimethyl sulfoxide (3.8 ml) solution of 2-tert-butyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-72) (77 mg, 249 μmol), followed by stirring at 90° C. for 11 hours. After cooling, the reaction liquid was diluted with ethyl acetate, this was washed with saturated brine and 1 N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=8:1→4:1, v/v) to obtain the entitled compound (98 mg, 75%) as a colorless oil.

Workup

temperatureAfter cooling
customthe reaction liquid
washthis was washed with saturated brine and 1 N hydrochloric acid
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (n-hexane

Sources & evidence

ORD record: ord-8d15c92b38f44c1eb3f0c734630f170e
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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