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

HRID 17402Notes

Reaction equation

F[C:2]1[C:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:4]([CH3:16])[C:5]([C:14]#[N:15])=[C:6]2[C:10]=1[O:9][C:8]([N:11]([CH3:13])[CH3:12])=[N:7]2.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.ClCCl>[CH3:12][N:11]([CH3:13])[C:8]1[O:9][C:10]2[C:6](=[C:5]([C:14]#[N:15])[C:4]([CH3:16])=[C:3]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:2]=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: 150 °C

Procedure

7-Fluoro-2-(dimethylamino)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-132) (0.18 g, 0.61 mmol) was suspended in dimethyl sulfoxide (5 ml), then triethylamine (0.17 ml, 1.23 mmol) and (3S)-3-(dimethylamino)pyrrolidine (0.16 ml, 1.26 mmol) were added, followed by stirring in a sealed tube at an external temperature of about 150° C. for 4 hours. This was diluted with dichloromethane, washed with water and brine, 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=30:1), then diisopropyl ether was added, and the insoluble matter was collected by filtration to obtain a pale beige solid (78.5 mg, 33%).

Workup

washwashed with water and brine
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=30:1)
additiondiisopropyl ether was added
filtrationthe insoluble matter was collected by filtration

Sources & evidence

ORD record: ord-b45f8c6ea219484faa12f8677fab6b29
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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