Water → HCID 58724570, compound

HRID 1393046Notes

Reaction equation

HRID 1393046 reaction equation
[H-].[Na+].[CH3:3][C@:4]12[C:10]([CH3:12])([CH3:11])[C@H:7]([CH2:8][CH2:9]1)[CH2:6][C@@H:5]2[NH:13][C:14]([C:16]1[CH:17]=[N:18][N:19]([CH3:27])[C:20]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:15].[CH3:28]I.O>CN(C)C=O>[CH3:28][N:13]([C@H:5]1[CH2:6][C@@H:7]2[C:10]([CH3:11])([CH3:12])[C@@:4]1([CH3:3])[CH2:9][CH2:8]2)[C:14]([C:16]1[CH:17]=[N:18][N:19]([CH3:27])[C:20]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11851533HCID 11851533, compound

Product 1

HCID 58724570HCID 58724570, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil; 15 mg, 0.375 mmol) is added to a cooled (˜0° C.) solution of 1-methyl-5-phenyl-1H-pyrazole-4-carboxylic acid ((1R,2S,4R)-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-amide (of Example 91; 100 mg, 0.3 mmol) in dry dimethylformamide (10 mL) and the mixture is allowed to stir for 30 min. Methyl iodide (30 μL, 0.49 mmol) is added and the solution is stirred at room temperature until the reaction is complete, as judged by TLC. Water is added and the solution is extracted twice with ethyl acetate. The combined organic layers are washed with water and brine, dried (magnesium sulfate), filtered, evaporated, and purified by C-18 reversed phase HPLC with a gradient of 10-100% acetonitrile/water containing 0.1% TFA as a modifier to give 1-methyl-5-phenyl-1H-pyrazole-4-carboxylic acid methyl-((1R,2S,4R)-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-amide.

Workup

  1. stirringthe solution is stirred at room temperature until the reaction
  2. extractionthe solution is extracted twice with ethyl acetate
  3. washThe combined organic layers are washed with water and brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. custompurified by C-18

Sources & evidence

ORD record
ord-6e5ea55e0f5d4ea58eeddbf23fc80511
Source dataset
uspto-grants-2008_03
Patent number
US07345058B2

Reaction notes

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