Hydrochloric Acid → 1-(1-(1-(5,7-Difluoroquinolin-6-yl)ethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone

HRID 1892438Notes

Reaction equation

HRID 1892438 reaction equation
C([O:3][C:4]([C:6]1[N:11]=[C:10]2[N:12]([CH:15]([C:17]3[C:18]([F:28])=[C:19]4[C:24](=[CH:25][C:26]=3[F:27])[N:23]=[CH:22][CH:21]=[CH:20]4)[CH3:16])[N:13]=[N:14][C:9]2=[N:8][CH:7]=1)=[CH2:5])C.Cl>CO>[F:28][C:18]1[C:17]([CH:15]([N:12]2[C:10]3=[N:11][C:6]([C:4](=[O:3])[CH3:5])=[CH:7][N:8]=[C:9]3[N:14]=[N:13]2)[CH3:16])=[C:26]([F:27])[CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][CH:22]=[N:23]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 581905966-(1-(6-(1-Ethoxyvinyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)ethyl)-5,7-difluoroquinoline

Product 1

HCID 581905541-(1-(1-(5,7-Difluoroquinolin-6-yl)ethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanoneYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-(1-(6-(1-ethoxyvinyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)ethyl)-5,7-difluoroquinoline (100.0 mg, 0.24 mmol) and 3 N HCl (0.1 mL) in CH3OH (10 mL) was stirred at 50° C. for 2 hours. The solvent was removed under reduced pressure. The reaction mixture was concentrated in vacuo to give the title compound as yellow solid (80.0 mg, 96%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.23 (s, 1H), 9.01 (dd, 1H), 8.53 (d, 2H), 7.76 (d, 1H), 7.64 (dd, 1H), 6.87 (q, 1H), 2.49 (s, 3H), 2.40 (d, 3H). LCMS (method A): [MH]+=355, tR=5.36 min.

Workup

  1. customThe solvent was removed under reduced pressure
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-3c450a92e9194a8995e451786d9fea20
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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