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

HRID 885067Notes

Reaction equation

HRID 885067 reaction equation
[OH:1][CH:2]([C:4]1[N:8]=[CH:7][N:6]([C:9]2[N:10]=[CH:11][C:12]([O:25][CH3:26])=[C:13]3[C:17]([C:18](=[O:24])[C:19]([O:21]CC)=[O:20])=[CH:16][NH:15][C:14]=23)[N:5]=1)[CH3:3].C([O-])([O-])=O.[K+].[K+].Cl>CO.O>[OH:1][CH:2]([C:4]1[N:8]=[CH:7][N:6]([C:9]2[N:10]=[CH:11][C:12]([O:25][CH3:26])=[C:13]3[C:17]([C:18](=[O:24])[C:19]([OH:21])=[O:20])=[CH:16][NH:15][C:14]=23)[N:5]=1)[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 58026059ethyl 2-(7-(3-(1-hydroxyethyl)-1H-1,2,4-triazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate

Product 1

HCID 580260672-(7-(3-(1-hydroxyethyl)-1H-1,2,4-triazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acidYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 2-(7-(3-(1-hydroxyethyl)-1H-1,2,4-triazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate (100 mg, 0.278 mmol) and K2CO3 (77 mg, 0.557 mmol) were dissolved in MeOH (2 mL) and water (2 mL). The mixture was stirred at room temperature overnight, and neutralized with 1N HCl to pH 3. All solvents were removed and the residue was purified by prep. HPLC to give 2-(7-(3-(1-hydroxyethyl)-1H-1,2,4-triazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid (46 mg, 0.139 mmol, 49.9% yield). LCMS: m/z 332.1 (M+H)+, 1.17 min (method 8).

Workup

  1. customAll solvents were removed
  2. customthe residue was purified by prep

Sources & evidence

ORD record
ord-d58bc6c71b0f4e8ab0f6ffcb5bfcfca3
Source dataset
uspto-grants-2012_08
Patent number
US08242124B2

Reaction notes

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