Triethylamine → HCID 52913370, compound

HRID 540748Notes

Reaction equation

HRID 540748 reaction equation
[F:1][C:2]([F:9])([F:8])[CH2:3][S:4](Cl)(=[O:6])=[O:5].[CH2:10]([N:12]1[C:16]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[CH:15][C:14]([C:28]2[CH:29]=[C:30]([C:34]([NH2:37])([CH3:36])[CH3:35])[CH:31]=[CH:32][CH:33]=2)=[N:13]1)[CH3:11].C(N(CC)CC)C>ClCCl>[CH2:10]([N:12]1[C:16]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:26])([F:25])[F:27])=[CH:20][CH:19]=2)=[CH:15][C:14]([C:28]2[CH:29]=[C:30]([C:34]([NH:37][S:4]([CH2:3][C:2]([F:9])([F:8])[F:1])(=[O:6])=[O:5])([CH3:36])[CH3:35])[CH:31]=[CH:32][CH:33]=2)=[N:13]1)[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 67111054HCID 67111054, compound

Product 1

HCID 52913370HCID 52913370, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

2,2,2-trifluoroethanesulfonyl chloride (0.83 mL, 7.7 mmol, 1.5 equiv) was added to a solution of 2-(3-{1-ethyl-5-[4-(trifluoromethyl)phenoxy]-1H-pyrazol-3-yl}phenyl)propan-2-amine (2.0 g, 5.1 mmol, 1 equiv) and triethylamine (1.1 mL, 7.7 mmol, 1.5 equiv) in dichloromethane (51 mL) at −78° C. The reaction mixture was stirred at −78° C. for 10 minutes, and then the cooling bath was removed. After stirring for 20 minutes, the reaction mixture was partitioned between dichloromethane and citric acid solution (1 M). The organic layer was dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated. The residue was purified by flash-column chromatography on silica gel (hexanes, grading to 50% ethyl acetate-hexanes) to afford N-[1-(3-{1-ethyl-5-[4-(trifluoromethyl)phenoxy]-1H-pyrazol-3-yl}phenyl)-1-methylethyl]-2,2,2-trifluoroethanesulfonamide (2.04 g, 74%) as a white solid. Calcd (M+1)+: 536.1. Found: 536.1. 1H NMR (600 MHz, cdcl3) δ 7.92 (s, 1H), 7.70 (d, J=7.3, 1H), 7.65 (d, J=8.7, 2H), 7.48-7.39 (m, 2H), 7.22 (d, J=8.6, 2H), 6.06 (s, 1H), 5.01 (s, 1H), 4.11 (q, J=7.3, 2H), 3.42 (q, J=8.9, 2H), 1.83 (s, 6H), 1.45 (t, J=7.3, 3H).

Workup

  1. customthe cooling bath was removed
  2. stirringAfter stirring for 20 minutes
  3. customthe reaction mixture was partitioned between dichloromethane and citric acid solution (1 M)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationThe dried solution was filtered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by flash-column chromatography on silica gel (hexanes, grading to 50% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-a31a93973c7440f99d6d41686154971d
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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