Potassium Carbonate → HCID 10405905, compound

HRID 720437Notes

Reaction equation

HRID 720437 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:24])[N:15]([CH2:18][CH2:19][O:20]C(=O)C)[CH2:16][CH2:17][C:12]=3[C:11]([C:25]([F:28])([F:27])[F:26])=[N:10]2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[OH:20][CH2:19][CH2:18][N:15]1[CH2:16][CH2:17][C:12]2[C:11]([C:25]([F:28])([F:26])[F:27])=[N:10][N:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[C:13]=2[C:14]1=[O:24]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 69596872HCID 69596872, compound

Product 1

HCID 10405905HCID 10405905, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Part B: Acetic acid 2-[1-(4-methoxy-phenyl)-7-oxo-3-trifluoromethyl-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-ethyl ester (1.26 g, 3.17 mmol) was dissolved in methanol (100 mL) and water (5 mL). Potassium carbonate (1.31 g, 9.52 mmol) was added, and the reaction was stirred overnight at rt. The reaction was concentrated, quenched with water (250 mL), extracted with ethyl acetate (3×250 mL), washed with brine (1×100 mL), dried over MgSO4, concentrated, and purified by flash chromatography with 0–100% ethyl acetate/hexanes gradient as eluent to afford the title compound (1.01 g, 90%): 1HNMR(CDCl3) δ 7.45 (d, j=9.2 Hz, 2H), 6.96 (d, j=8.7 Hz, 2H), 3.84 (s, 3H), 3.82–3.77 (m, 4H), 3.66 (t, j=5.1 Hz, 2H), 3.03 (t, j=6.8 Hz, 2H) ppm; Mass Spec 356.3(M+H)+.

Workup

  1. concentrationThe reaction was concentrated
  2. customquenched with water (250 mL)
  3. extractionextracted with ethyl acetate (3×250 mL)
  4. washwashed with brine (1×100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. custompurified by flash chromatography with 0–100% ethyl acetate/hexanes gradient as eluent

Sources & evidence

ORD record
ord-5a96e28298e241b4baed3f63d92f7036
Source dataset
uspto-grants-2006_11
Patent number
US07135469B2

Reaction notes

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