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Triethylamine → HCID 46830922, compound

HRID 1848346
Notes
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Reaction equation

HRID 1848346 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 61277Isopropyl isocyanate2×HCID 46830920HCID 46830920, compound2×

Product 1

HCID 46830922HCID 46830922, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

  1. stirringthe reaction mixture was shaken at 65° C. for another 24 H
  2. customThe solvent was evaporated
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes