Water → HCID 58958620, compound

HRID 915606Notes

Reaction equation

HRID 915606 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([NH:15][C:16]2[N:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])[N:19]=[C:18]([CH3:28])[C:17]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11].I[CH3:36].O>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:15]([CH3:36])[C:16]2[N:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])[N:19]=[C:18]([CH3:28])[C:17]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69277802HCID 69277802, compound

Product 1

HCID 58958620HCID 58958620, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of NaH (60% dispersion in mineral oil; 0.28 g, 7 mmol) in DMF (10 mL) at rt was added a solution of methyl 5-methoxy-2-{[3-methyl-1-(2-methylphenyl)-4-phenyl-1H-pyrazol-5-yl]amino}benzoate (1.495 g, 3.5 mmol) in DMF (15 mL) dropwise. The mixture was stirred for 0.5 h, and then iodomethane (0.88 mL, 14 mmol) was added. The reaction mixture was stirred at rt for 1 h. Water (100 mL) was cautiously added, and the mixture was extracted with ethyl acetate (25 mL×3). The combined organic phases were washed with a saturated solution of sodium bicarbonate (50 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (EtOAc/hexanes 1:12) to afford the title compound (1.18 g, 68%) as a pale yellow solid. 1H NMR (400 MHz, acetone-d6) δ 2.1 (s, 3H), 2.3 (s, 3H), 2.9 (s, 3H), 3.65 (s, 3H), 3.7 (s, 3H), 6.87-6.92 (m, 2H), 6.94-6.98 (m, 1H), 7.03-7.09 (m, 1H), 7.15-7.27 (m, 4H), 7.30-7.36 (m, 2H), 7.39-7.43 (m, 2H). ES-MS m/z 442.3 (MH+); HPLC RT (min) 3.96.

Workup

  1. stirringThe reaction mixture was stirred at rt for 1 h
  2. extractionthe mixture was extracted with ethyl acetate (25 mL×3)
  3. washThe combined organic phases were washed with a saturated solution of sodium bicarbonate (50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel flash chromatography (EtOAc/hexanes 1:12)

Sources & evidence

ORD record
ord-904836a7ae1f4978a0e6283bc2f21993
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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