Ethyl Acetate → HCID 25265727, compound

HRID 1094322Notes

Reaction equation

HRID 1094322 reaction equation
[NH:1]1[C:5]([C@@H:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[S:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=3)=[CH:10][CH:9]=2)[CH3:7])=[CH:4][CH:3]=[N:2]1.CC[O:26]C(C)=O>>[F:23][C:20]([F:22])([F:21])[C:18]1[N:19]=[C:15]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([C@H:6]([C:5]3[N:1]([OH:26])[N:2]=[CH:3][CH:4]=3)[CH3:7])=[CH:9][CH:10]=2)[S:16][CH:17]=1

Participants

3

Reactant 2

HCID 8857Ethyl Acetate2×HCID 86645974HCID 86645974, compound

Product 1

HCID 25265727HCID 25265727, compoundYield 67%

Procedure

To a solution of N-{4-[(1R)-1-(1H-pyrazol-5-yl)ethyl]phenyl}-4-(trifluoromethyl)-1,3-thiazol-2-amine (0.421 g, 1.24 mmol) in EtOAc (5 mL) m-CPBA (256 mg, 1.5 mmol) was added and the resulting mixture was stirred at room temperature overnight. The crude was diluted with EtOAc (10 ml), washed with water (2×10 ml) and dried over anhydrous Na2SO4. After solvent evaporation, the crude was purified by flash chromatography to give the pure 5-[(1R)-1-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)ethyl]-1H-pyrazol-1-ol (7) (0.295 g, 0.65 mmol) as a white solid (67%). [α]D=−28 (c=0.82; CH3OH); 1H-NMR (CD3OD): δ 9.40 (bs, 1H, NH); 7.55 (d, 1H, J=2.5 Hz); 7.40 (d, 2H, J=7 Hz); 7.35 (d, 2H, J=7 Hz); 7.15 (s, 1H), 6.25 (d, 1H, J=2.4 Hz); 3.80 (q, 1H, J=7 Hz); 1.60 (d, 3H, J=7 Hz).

Workup

  1. washwashed with water (2×10 ml)
  2. dry with materialdried over anhydrous Na2SO4
  3. customAfter solvent evaporation
  4. customthe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-ace79fab50864477a32c3f681dd54336
Source dataset
uspto-grants-2012_03
Patent number
US08133911B2

Reaction notes

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