Triethylamine → HCID 68585012, compound

HRID 17511Notes

Reaction equation

[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.F[C:17]1[C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:19]([CH3:30])[C:20]([C:28]#[N:29])=[C:21]2[C:25]=1[O:24][C:23]([CH2:26][OH:27])=[N: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:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[C:19]([CH3:30])[C:20]([C:28]#[N:29])=[C:21]3[C:25]=2[O:24][C:23]([CH2:26][OH:27])=[N:22]3)[CH2:4]1

Participants

Conditions

Temperature: 95 °C

Procedure

(3S)-3-(Dimethylamino)pyrrolidine (18.2 μl, 0.143 mmol) and triethylamine (26.7 μl, 0.191 mmol) were added to a dimethyl sulfoxide (0.5 ml) solution of 7-fluoro-2-hydroxymethyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-218) (27.0 mg, 0.096 mmol), followed by stirring in an oil bath at 95° C. for 3 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in chloroform (10 ml), and washed with saturated brine (10 ml). After drying over anhydrous sodium sulfate and concentration, the resulting residue was purified by preparative TLC (eluent, chloroform:methanol-10:1), and the eluate was purified in slurry with diethyl ether to obtain the entitled compound (4.00 mg, 11.1%) as a pale yellow solid.

Workup

customThe reaction liquid
concentrationwas concentrated under reduced pressure
dissolutionthe residue was dissolved in chloroform (10 ml)
washwashed with saturated brine (10 ml)
dry with materialAfter drying over anhydrous sodium sulfate and concentration
customthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol-10:1)
customthe eluate was purified in slurry with diethyl ether

Sources & evidence

ORD record: ord-fcff3104850c425fa239f47f37515515
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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