Hydrochloric Acid → methyl 1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazole-3-carboxylate

HRID 885060Notes

Reaction equation

HRID 885060 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[N:7][C:6]([N:9]2[CH:13]=[N:12][C:11]([C:14]#N)=[N:10]2)=[C:5]2[NH:16][CH:17]=[CH:18][C:4]=12.[C:19]([O-])([O-])=[O:20].[K+].[K+].Cl.C[OH:27]>O>[CH3:1][O:2][C:3]1[CH:8]=[N:7][C:6]([N:9]2[CH:13]=[N:12][C:11]([C:14]([O:20][CH3:19])=[O:27])=[N:10]2)=[C:5]2[NH:16][CH:17]=[CH:18][C:4]=12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 580260371-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazole-3-carbonitrile

Product 1

HCID 58026033methyl 1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazole-3-carboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(4-Methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazole-3-carbonitrile (1 g, 4.16 mmol) and K2CO3 (0.863 g, 6.24 mmol) were combined in MeOH (20 mL) and water (20 mL). The mixture was stirred at room temperature overnight. The mixture was neutralized with 1N HCl to pH=3. The precipitate was collected by filtration to give methyl 1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazole-3-carboxylate (1.03 g, 3.77 mmol, 91% yield). LCMS: m/z 274.2 (M+H)+, 1.63 min (method 8). 1H NMR (500 MHz, MeOD) d ppm 9.22 (s, 1H) 7.47 (s, 1H) 7.39 (d, J=3.05 Hz, 1H) 6.62 (d, J=3.05 Hz, 1H) 4.03 (s, 3H) 4.00 (s, 3H).

Workup

  1. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-2a584d40fc13432eac1f9ff711f1f8fc
Source dataset
uspto-grants-2012_08
Patent number
US08242124B2

Reaction notes

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