Hydrochloric Acid → 2-(7-(3-(hydroxymethyl)-1H-1,2,4-triazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid

HRID 885063Notes

Reaction equation

HRID 885063 reaction equation
[OH:1][CH2:2][C:3]1[N:7]=[CH:6][N:5]([C:8]2[N:9]=[CH:10][C:11]([O:24][CH3:25])=[C:12]3[C:16]([C:17](=[O:23])[C:18]([O:20]CC)=[O:19])=[CH:15][NH:14][C:13]=23)[N:4]=1.C([O-])([O-])=O.[K+].[K+].Cl>CO.O>[OH:1][CH2:2][C:3]1[N:7]=[CH:6][N:5]([C:8]2[N:9]=[CH:10][C:11]([O:24][CH3:25])=[C:12]3[C:16]([C:17](=[O:23])[C:18]([OH:20])=[O:19])=[CH:15][NH:14][C:13]=23)[N:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 58026036ethyl 2-(7-(3-(hydroxymethyl)-1H-1,2,4-triazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate

Product 1

HCID 580260572-(7-(3-(hydroxymethyl)-1H-1,2,4-triazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 2-(7-(3-(hydroxymethyl)-1H-1,2,4-triazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate (70 mg, 0.203 mmol) and K2CO3 (56.0 mg, 0.405 mmol) were dissolved in MeOH (2 mL) and water (2.000 mL). The mixture was stirred at room temperature overnight, and neutralized with 1N HCl to pH 3. All solvents were removed under vacuum to give 2-(7-(3-(hydroxymethyl)-1H-1,2,4-triazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid. LCMS: m/z 318.2 (M+H)+, 1.04 min (method 8).

Workup

  1. customAll solvents were removed under vacuum

Sources & evidence

ORD record
ord-4b436dae6e5f47699b4d2e560b894283
Source dataset
uspto-grants-2012_08
Patent number
US08242124B2

Reaction notes

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