Triethylamine → HCID 68587759, compound

HRID 17348Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

2-[(Benzyloxy)methyl]-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-90) (70 mg, 0.19 mmol) was dissolved in dimethyl sulfoxide (1.4 ml), triethylamine (63 μl, 0.45 mmol) and (3S)-3-(dimethylamino)pyrrolidine (29 μl, 0.23 mmol) were added, followed by stirring at 90° C. for 4 hours under nitrogen atmosphere. After cooling to room temperature, ethyl acetate was added, followed by fractionation with water. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated away and the resulting residue was subjected to preparative, thin-layer silica gel column, chromatography, eluted with a mixed solvent of chloroform/methanol (10:1, v/v) to obtain the entitled compound (46 mg, 52%) as a yellow oily substance.

Workup

temperatureAfter cooling to room temperature
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated away
washeluted with a mixed solvent of chloroform/methanol (10:1

Sources & evidence

ORD record: ord-c39f998010154943a06b7a90bc4ff72a
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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