Triethylamine → HCID 68585189, compound

HRID 17477Notes

Reaction equation

[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.[CH2:9](N(CC)CC)C.F[C:17]1[C:18]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[C:19]([CH3:36])[C:20]([C:34]#[N:35])=[C:21]2[C:25]=1[O:24][C:23]([NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)(C)[NH:22]2>CS(C)=O>[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][N:5]([C:17]2[C:18]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[C:19]([CH3:36])[C:20]([C:34]#[N:35])=[C:21]3[C:25]=2[O:24][C:23]([N:27]([CH3:9])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[N:22]3)[CH2:4]1

Participants

Conditions

Temperature: 95 °C

Procedure

(3S)-3-(Dimethylamino)pyrrolidine (63.2 μl, 0.498 mmol) and triethylamine (81.7 μl, 0.586 mmol) were added to a dimethyl sulfoxide (3 ml) solution of 7-fluoro-5-methyl-2-methylpyridin-2-ylamino-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-189) (105 mg, 0.293 mmol), followed by stirring in an oil bath at 95° C. for 2 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in chloroform (50 ml), washed with saturated brine (50 ml). After drying over anhydrous sodium sulfate and concentration, the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=20:1), and the obtained eluate was recrystallized from isopropanol to obtain the entitled compound (35.0 mg, 26.4%) as a colorless solid.

Workup

customThe reaction liquid
concentrationwas concentrated under reduced pressure
dissolutionthe residue was dissolved in chloroform (50 ml)
washwashed with saturated brine (50 ml)
dry with materialAfter drying over anhydrous sodium sulfate and concentration
customthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=20:1)
customthe obtained eluate was recrystallized from isopropanol

Sources & evidence

ORD record: ord-f9b627c6ef7c4f7dad3ebeb10f0f4ec0
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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