Sodium hydride → HCID 86638508, compound

HRID 216405Notes

Reaction equation

HRID 216405 reaction equation
[F:1][C:2]([F:30])([F:29])/[C:3](/[C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH:28]=[CH:27][CH:26]=[N:25]2)=[CH:20][CH:19]=1)=[CH:4]\[C:5]1[NH:6][CH:7]=[C:8]([CH2:10][C:11]2([C:14]([F:17])([F:16])[F:15])[CH2:13][CH2:12]2)[N:9]=1.[H-].[Na+].[CH3:33][N:34]([CH3:39])[S:35](Cl)(=[O:37])=[O:36]>O1CCCC1>[CH3:33][N:34]([CH3:39])[S:35]([N:6]1[CH:7]=[C:8]([CH2:10][C:11]2([C:14]([F:15])([F:16])[F:17])[CH2:12][CH2:13]2)[N:9]=[C:5]1/[CH:4]=[C:3](/[C:18]1[CH:19]=[CH:20][C:21]([N:24]2[CH:28]=[CH:27][CH:26]=[N:25]2)=[CH:22][CH:23]=1)\[C:2]([F:1])([F:29])[F:30])(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 83372Dimethylsulphamoyl chlorideHCID 178506310HCID 178506310, compound

Product 1

HCID 86638508HCID 86638508, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 250-mL round-bottom flask, a mixture of 1-{4-[(Z)-1-(trifluoromethyl)-2-(4-{[1-(trifluoromethyl)cyclopropyl]methyl}-1H-imidazol-2-yl)vinyl]phenyl}-1H-pyrazole (5.05 g, 11.8 mmol) and 60 wt % sodium hydride (0.89 g, 22 mmol) were mixed with tetrahydrofuran (80 mL). After bubbling ceased, dimethylsulfamoyl chloride (2.6 mL, 24.26 mmol) was added, and the reaction mixture was stirred overnight. The reaction mixture was quenched with water and extracted with diethyl ether. The combined organic extracts were washed with brine, dried (potassium carbonate), and concentrated in vacuo to afford an orange solid. Chromatography over silica eluting with 25-40% ethyl acetate/hexanes afforded N,N-dimethyl-4-{[1-(trifluoromethyl)cyclopropyl]methyl}-2-{(1Z)-3,3,3-trifluoro-2-[4-(1H-pyrazol-1-yl)phenyl]prop-1-en-1-yl}-1H-imidazole-1-sulfonamide, as a yellow solid.

Workup

  1. customAfter bubbling
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with diethyl ether
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (potassium carbonate)
  6. concentrationconcentrated in vacuo
  7. customto afford an orange solid

Sources & evidence

ORD record
ord-b48b817332ba482b957ab0ae12ab524d
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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