Triethylamine → HCID 68587500, compound

HRID 17359Notes

Reaction equation

[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[O:11][C:12]3[C:13](=[C:15]([C:27]#[N:28])[C:16]([CH3:26])=[C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:18]=3F)[N:14]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(N(CC)CC)C.[CH3:36][N:37]([CH3:43])[C@H:38]1[CH2:42][CH2:41][NH:40][CH2:39]1>CS(C)=O>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[O:11][C:12]3[C:13](=[C:15]([C:27]#[N:28])[C:16]([CH3:26])=[C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:18]=3[N:40]3[CH2:41][CH2:42][C@H:38]([N:37]([CH3:43])[CH3:36])[CH2:39]3)[N:14]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

2-(1-Acetylpiperidin-4-yl)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-104) (0.23 g, 0.61 mmol) was dissolved in dimethyl sulfoxide (7 ml), triethylamine (0.18 ml, 1.30 mmol) and (3S)-3-(dimethylamino)pyrrolidine (85.0 μl, 0.67 mmol) were added, followed by stirring an external temperature of about 90° C. for 4 hours. After dilution with ethyl acetate, this was washed with water, dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure and the resulting residue was purified by silica gel column chromatography (silica gel 10 g, dichloromethane:methanol=30:1) to obtain a colorless oil (73 mg, 25%). This was dissolved in dioxane and freeze-dried into solid.

Workup

washAfter dilution with ethyl acetate, this was washed 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 (silica gel 10 g, dichloromethane:methanol=30:1)

Sources & evidence

ORD record: ord-67871b1c31a9404ca1234b8028fc371e
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

Loading…