Triethylamine → 2-(dimethylamino)-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile

HRID 17442Notes

Reaction equation

[CH3:1][N:2]([CH3:22])[C:3]1[O:4][C:5]2[C:6](=[C:8]([C:20]#[N:21])[C:9]([CH3:19])=[C:10]([C:13]3[N:14]=[C:15]([CH3:18])[S:16][CH:17]=3)[C:11]=2F)[N:7]=1.C(N(CC)CC)C.[CH3:30][N:31]([CH3:37])[C@H:32]1[CH2:36][CH2:35][NH:34][CH2:33]1>CS(C)=O.C(OCC)(=O)C>[CH3:1][N:2]([CH3:22])[C:3]1[O:4][C:5]2[C:6](=[C:8]([C:20]#[N:21])[C:9]([CH3:19])=[C:10]([C:13]3[N:14]=[C:15]([CH3:18])[S:16][CH:17]=3)[C:11]=2[N:34]2[CH2:35][CH2:36][C@H:32]([N:31]([CH3:37])[CH3:30])[CH2:33]2)[N:7]=1

Participants

Conditions

Temperature: 110 °C

Procedure

2-(Dimethylamino)-7-fluoro-5-methyl-6-(2-methyl-1,3-thiazol-4-yl)-1,3-benzoxazole-4-carbonitrile (I-171) (0.44 g, 1.39 mmol) was suspended in dimethyl sulfoxide (10 ml), then triethylamine (0.42 ml 3.03 mmol) and (3S)-3-(dimethylamino)pyrrolidine (0.38 ml, 3.00 mmol) were added, followed by stirring at an external temperature of about 110° C. for 4 hours. This was diluted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=50:1 to 10:1) to obtain a brown amorphous substance (0.51 g, 83%).

Workup

washwashed with water
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated away under reduced pressure
customthe resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=50:1 to 10:1)
customto obtain a brown amorphous substance (0.51 g, 83%)

Sources & evidence

ORD record: ord-fb891ccb48cb47bb8e581d1314cd2516
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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