Ammonium Chloride → HCID 52914043, compound

HRID 540765Notes

Reaction equation

HRID 540765 reaction equation
[CH3:1][Mg]Br.[CH2:4]([N:6]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]=[O:19])=[CH:14][CH:13]=2)=[CH:9][C:8]([C:20]2[CH:21]=[C:22]([C:26]([NH:29][S:30]([CH2:33][C:34]([F:37])([F:36])[F:35])(=[O:32])=[O:31])([CH3:28])[CH3:27])[CH:23]=[CH:24][CH:25]=2)=[N:7]1)[CH3:5].[Cl-].[NH4+]>O1CCCC1>[CH2:4]([N:6]1[C:10]([O:11][C:12]2[CH:13]=[CH:14][C:15]([CH:18]([OH:19])[CH3:1])=[CH:16][CH:17]=2)=[CH:9][C:8]([C:20]2[CH:21]=[C:22]([C:26]([NH:29][S:30]([CH2:33][C:34]([F:37])([F:35])[F:36])(=[O:31])=[O:32])([CH3:28])[CH3:27])[CH:23]=[CH:24][CH:25]=2)=[N:7]1)[CH3:5]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 52913937HCID 52913937, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 52914043HCID 52914043, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methylmagnesium bromide (3.00 M in diethyl ether, 0.135 mL, 0.404 mmol, 2.00 equiv) was added to a solution of N-(1-{3-[1-ethyl-5-(4-formylphenoxy)-1H-pyrazol-3-yl]phenyl}-1-methylethyl)-2,2,2-trifluoroethanesulfonamide (100 mg, 0.202 mmol, 1 equiv) in tetrahydrofuran (2.0 mL) at 0° C. The reaction mixture was stirred at 0° C. for 5 minutes, then was treated with saturated aqueous ammonium chloride solution. The biphasic mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride solution, and the washed solution was dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated. The residue was purified by flash-column chromatography (hexanes, grading to 90% ethyl acetate-hexanes) to afford N-[1-(3-{1-ethyl-5-[4-(1-hydroxyethyl)phenoxy]-1H-pyrazol-3-yl}phenyl)-1-methylethyl]-2,2,2-trifluoroethanesulfonamide (79 mg, 77%). Calcd (M+1)+: 512.2. Found: 512.1.

Workup

  1. customThe biphasic mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialthe washed solution was dried over sodium sulfate
  4. filtrationThe dried solution was filtered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by flash-column chromatography (hexanes, grading to 90% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-ee5309adcacb4886b63ad1199dbd513e
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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