Potassium Carbonate → 2-(4-methoxy-7-(3-pivalamido-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid

HRID 1157788Notes

Reaction equation

HRID 1157788 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[N:7][C:6]([N:9]2[CH:13]=[N:12][C:11]([NH:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[N:10]2)=[C:5]2[NH:21][CH:22]=[C:23]([C:24](=[O:29])[C:25]([O:27]C)=[O:26])[C:4]=12.C([O-])([O-])=O.[K+].[K+]>O.CO>[CH3:1][O:2][C:3]1[CH:8]=[N:7][C:6]([N:9]2[CH:13]=[N:12][C:11]([NH:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[N:10]2)=[C:5]2[NH:21][CH:22]=[C:23]([C:24](=[O:29])[C:25]([OH:27])=[O:26])[C:4]=12

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 68694028methyl 2-(4-methoxy-7-(3-pivalamido-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate

Product 1

HCID 595114512-(4-methoxy-7-(3-pivalamido-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acidYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of methyl 2-(4-methoxy-7-(3-pivalamido-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate (40 mg, 0.100 mmol) in water (1 mL) and MeOH (1 mL) was added K2CO3 (83 mg, 0.599 mmol) at room temperature. The reaction mixture was stirred overnight at room temperature. MeOH was removed under reduced pressure. The water layer was acidified to PH=5-6 using 1N HCl and concentrated under reduced pressure. The resulting residue was washed with water, filtered and dried to give 2-(4-methoxy-7-(3-pivalamido-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid (30 mg, 78%) as white solid. LCMS: m/e 387.18 (M+H)+, ret time 2.46 min (method 4).

Workup

  1. customMeOH was removed under reduced pressure
  2. concentrationconcentrated under reduced pressure
  3. washThe resulting residue was washed with water
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-3f0e307d6fac4b3f9aca4f94dd373572
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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