Triethylamine → HCID 68585972, compound

HRID 17482Notes

Reaction equation

F[C:2]1[C:3]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:4]([CH3:19])[C:5]([C:17]#[N:18])=[C:6]2[C:10]=1[O:9][C:8]([N:11]1[CH2:14][CH:13]([CH2:15][OH:16])[CH2:12]1)=[N:7]2.C(N(CC)CC)C.[CH3:33][N:34]([CH3:40])[C@H:35]1[CH2:39][CH2:38][NH:37][CH2:36]1>CS(C)=O>[CH3:33][N:34]([CH3:40])[C@H:35]1[CH2:39][CH2:38][N:37]([C:2]2[C:3]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:4]([CH3:19])[C:5]([C:17]#[N:18])=[C:6]3[C:10]=2[O:9][C:8]([N:11]2[CH2:14][CH:13]([CH2:15][OH:16])[CH2:12]2)=[N:7]3)[CH2:36]1

Participants

Conditions

Temperature: 150 °C

Procedure

7-Fluoro-2-[3-(hydroxymethyl)azetidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-192) (220 mg, 0.37 mmol) was dissolved in dimethyl sulfoxide (5 ml), then triethylamine (166 μl, 1.19 mmol) and (3S)-3-(dimethylamino)pyrrolidine (159 μl, 1.25 mmol) were added, followed by stirring in a sealed tube at 150° C. for 19 hours. After cooling, concentration under reduced pressure, dilution with methylene chloride and washing with water, the organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure. The resulting residue was subjected to preparative silica gel column chromatography. The eluate with chloroform/methanol (10:1, v/v) gave the entitled compound (208 mg, 74%) as a white amorphous substance.

Workup

temperatureAfter cooling
concentrationconcentration under reduced pressure, dilution with methylene chloride
washwashing with water
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record: ord-55aa904223ef4181b5bff9f95521f21f
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

Loading…