HCID 10432527, compound → HCID 10024597, compound

HRID 720436Notes

Reaction equation

HRID 720436 reaction equation
C[Mg]Br.C(OC(=O)[CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C:14]2[C:17]([C:28]([F:31])([F:30])[F:29])=[N:18][N:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[C:13]=2[C:12]1=[O:32])C>O1CCCC1>[OH:26][C:23]([CH3:24])([CH3:22])[CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C:14]2[C:17]([C:28]([F:31])([F:29])[F:30])=[N:18][N:19]([C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[C:13]=2[C:12]1=[O:32]

Participants

4

Reactant 2

HCID 10432527HCID 10432527, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 10024597HCID 10024597, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3M methylmagnesium bromide (0.682 g, 2.05 mmol) was added to 4-[1-(4-methoxy-phenyl)-7-oxo-3-trifluoromethyl-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-butyric acid ethyl ester (0.348 g, 0.818 mmol) dissolved in tetrahydrofuran (10 mL). The reaction was stirred at rt overnight. The reaction was quenched with 1N hydrochloric acid (50 mL), extracted with ethyl acetate (3×50 mL), washed with brine (1×50 mL), dried over MgSO4, concentrated, and purified by flash chromatography using 0–100% ethyl acetate/hexanes gradient as the eluent to afford 0.111 g (34%, based on recovered starting material): 1H NMR (CDCl3) δ 7.45 (d, j=9.2 Hz, 2H), 6.96 (d, j=8.7 Hz, 2H), 3.84 (s, 3H), 3.69 (t, j=6.8 Hz, 2H), 3.50(t, j=7.4 Hz, 2H), 3.00(t, j=6.8 Hz, 2H), 1.75–1.62 (m, 2H), 1.49–1.41 (m, 2H), 1.21 (s, 6H) ppm; Mass Spec (M+H)+ 412.3.

Workup

  1. customThe reaction was quenched with 1N hydrochloric acid (50 mL)
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washwashed with brine (1×50 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography
  7. customto afford
  8. custom0.111 g (34%, based on recovered starting material)

Sources & evidence

ORD record
ord-f796958a99ca4b6e8e730f65a35026c9
Source dataset
uspto-grants-2006_11
Patent number
US07135469B2

Reaction notes

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