Triethylamine → HCID 46830922, compound

HRID 1848346Notes

Reaction equation

[OH:1][CH2:2][C:3]1([C:6]2[N:24]=[C:9]3[C:10]([O:22][CH3:23])=[CH:11][CH:12]=[C:13]([C:14]4[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=4)[C:17]#[N:18])[N:8]3[N:7]=2)[CH2:5][CH2:4]1.CCN(CC)CC.[CH:32]([N:35]=[C:36]=[O:37])([CH3:34])[CH3:33]>CC#N>[C:17]([C:16]1[CH:15]=[C:14]([C:13]2[N:8]3[N:7]=[C:6]([C:3]4([CH2:2][O:1][C:36](=[O:37])[NH:35][CH:32]([CH3:34])[CH3:33])[CH2:5][CH2:4]4)[N:24]=[C:9]3[C:10]([O:22][CH3:23])=[CH:11][CH:12]=2)[CH:21]=[CH:20][CH:19]=1)#[N:18]

Participants

Conditions

Temperature: 65 °C

Procedure

Under an argon atmosphere 3-[2-(1-Hydroxymethyl-cyclopropyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-benzonitrile (compound 150) (0.03 g, 0.08 mmol) was dissolved in CH3CN (1 mL). Et3N (0.005 mL) and isopropyl isocyanate (0.04 mL) were added and the reaction mixture was shaken at 65° C. for 20 H. Et3N (0.005 mL) and isopropyl isocyanate (0.04 mL) were added again and the reaction mixture was shaken at 65° C. for another 24 H. The solvent was evaporated and the crude product was purified by flash chromatography on silica using DCM:MeOH 99:1 as eluent to afford the title compound as a solid.

Workup

stirringthe reaction mixture was shaken at 65° C. for another 24 H
customThe solvent was evaporated
customthe crude product was purified by flash chromatography on silica

Sources & evidence

ORD record: ord-42236cc6ffe54641b2c0f6318c31aee8
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952162B2

Reaction notes

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