HCID 57590905, compound → HCID 57590880, compound

HRID 1783759Notes

Reaction equation

HRID 1783759 reaction equation
C(OC(=O)[NH:7][CH2:8]/[CH:9]=[CH:10]/[C:11]1[C:20]2[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[C:14]2=[N:22][NH:23][C:24](=[O:25])[N:13]2[CH:12]=1)(C)(C)C>CC#N.C(O)(C(F)(F)F)=O>[NH2:7][CH2:8]/[CH:9]=[CH:10]/[C:11]1[C:20]2[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[C:14]2=[N:22][NH:23][C:24](=[O:25])[N:13]2[CH:12]=1

Participants

4

Reactant 1

HCID 57590905HCID 57590905, compound

Product 1

HCID 57590880HCID 57590880, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-butyl[(2E)-3-(9-chloro-3-oxo-2,3-dihydro[1,2,4]triazolo[3,4-a]isoquinolin-6-yl)prop-2-en-1-yl]carbamate (3-10) was dissolved in CH3CN (10 mL) with 0.1% TFA present. The resulted solution was irradiated in microwave at 150° C. for 5 minutes. LCMS showed only product. The crude mixture was purified with reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA) to afford the desired product 3-11. 1H NMR (500 MHz, CD3OD) δ 8.29 (d, 1H, J=2.9 Hz), 7.90 (d, 1H, J=8.5 Hz), 7.78-7.64 (m, 2H), 7.14 (d, 1H, J=16.5 Hz), 6.30 (dt, 1H, J=16.5 , 7.0 Hz), 3.83 (d, 2H, J=7.0 Hz). LRMS m/z (M+H) 275.1 found, 275.1 required.

Workup

  1. customThe resulted solution was irradiated in microwave at 150° C. for 5 minutes
  2. customThe crude mixture was purified with reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA)

Sources & evidence

ORD record
ord-e0f75c4e6bde457c863d63acf4a87886
Source dataset
uspto-grants-2009_03
Patent number
US07501435B2

Reaction notes

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