Water → HCID 52913486, compound

HRID 540801Notes

Reaction equation

HRID 540801 reaction equation
[O:1]1[CH:5]=[C:4]([CH2:6][N:7]2[C:11]([O:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)=[CH:10][C:9]([C:23]3[CH:24]=[C:25]([C:29]4([NH2:33])[CH2:32][O:31][CH2:30]4)[CH:26]=[CH:27][CH:28]=3)=[N:8]2)[N:3]=[CH:2]1.[F:34][C:35]([F:42])([F:41])[CH2:36][S:37](Cl)(=[O:39])=[O:38].O>C(Cl)Cl>[F:22][C:19]([F:20])([F:21])[C:16]1[CH:17]=[CH:18][C:13]([O:12][C:11]2[N:7]([CH2:6][C:4]3[N:3]=[CH:2][O:1][CH:5]=3)[N:8]=[C:9]([C:23]3[CH:24]=[C:25]([C:29]4([NH:33][S:37]([CH2:36][C:35]([F:42])([F:41])[F:34])(=[O:39])=[O:38])[CH2:32][O:31][CH2:30]4)[CH:26]=[CH:27][CH:28]=3)[CH:10]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 67110819HCID 67110819, compound

Product 1

HCID 52913486HCID 52913486, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 3-{3-[1-(1,3-oxazol-4-ylmethyl)-5-(4-trifluoromethylphenoxy)-1H-pyrazol-3-yl]phenyl}oxetan-3-amine (35 mg, 0.077 mmol) in 1 mL of CH2Cl2 was cooled in an ice bath. To the solution was added TEA (21 uL, 0.15 mmol) and 2,2,2-trifluoroethylsulfonyl chloride (12 uL, 0.12 mmol) and the solution was stirred for 30 min. Water was added and the organic phase was washed with brine, died over Na2SO4, filtered, and the solvent was removed under reduced pressure. The residue was chromatographed on a 12 g silica gel column using 0-5% MeOH:CHCl3 over 16 min at 30 mL/min. Product containing fractions were combined and the solvent was removed under reduced pressure to give N-(3-{3-[5-(4-trifluoromethylphenoxy)-1-(1,3-oxazol-4-ylmethyl)-1H-pyrazol-3-yl]phenyl}oxetan-3-yl)-2,2,2-trifluoroethanesulfonamide as a foam. Calcd (M+1)+: 603.1131. found 603.1153. 1H NMR (400 MHz, CDCl3) δ 7.80 (s, 1H), 7.78 (d, J=7, 1H), 7.65 (d, J=7, 2H), 7.61 (s, 1H), 7.49 (1, J=7, 1H), 7.37 (d, J=7, 2H), 7.28 (d, J=7, 2H), 7.09 (s, 1H), 6.08 (s, 1H), 6.05 (s, 1H), 5.44 (s, 2H), 5.23 (d, J=7, 2H), 5.05 (d, J=7, 2H), 3.03 (q, J=9, 2H).

Workup

  1. washthe organic phase was washed with brine
  2. filtrationfiltered
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was chromatographed on a 12 g silica gel column
  5. waitCHCl3 over 16 min at 30 mL/min
  6. additionProduct containing fractions
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e00eed7a2d504702bede0aff1abac8ed
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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