Ethyl Acetate → HCID 25265729, compound

HRID 1094325Notes

Reaction equation

HRID 1094325 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][N:3]=[N:2]1.CC[O:26]C(C)=O>>[F:22][C:20]([F:23])([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]=[N:3][CH:4]=3)[CH3:7])=[CH:9][CH:10]=2)[S:16][CH:17]=1

Participants

3

Reactant 2

HCID 8857Ethyl Acetate2×HCID 178461690HCID 178461690, compound

Product 1

HCID 25265729HCID 25265729, compoundYield 40%

Procedure

To a solution of N-{4-[(1R)-1-(1H-1,2,3-triazol-5-yl)ethyl]phenyl}-4-(trifluoromethyl)-1,3-thiazol-2-amine (0.06 g, 0.18 mmol) in EtOAc (10 ml) m-CPBA (43 mg, 0.25 mmol) was added and the resulting mixture stirred at room temperature overnight. EtOAc (10 ml) was added and the organic layer was washed with water (2×10 ml) and dried over anhydrous Na2SO4 to give, after solvent evaporation, a crude which, by purification by flash chromatography (EtOAc/CH3OH 7:3) afforded the pure 5-[(1R)-1-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)ethyl]-1H-1,2,3-triazol-1-ol (9) (0.025 g, 0.072 mmol) as a transparent oil (40%). [α]D=−19 (c=1; CH3OH); 1H-NMR (CD3OD): δ 9.40 (bs, 1H, NH), 7.40 (d, 2H, J=7 Hz), 7.35 (d, 2H, J=7 Hz), 7.15 (s, 1H), 7.40 (s, 1H), 3.70 (q, 1H, J=7 Hz), 1.55 (d, 3H, J=7 Hz).

Workup

  1. washthe organic layer was washed with water (2×10 ml)
  2. dry with materialdried over anhydrous Na2SO4
  3. customto give
  4. customafter solvent evaporation
  5. customa crude which, by purification by flash chromatography (EtOAc/CH3OH 7:3)

Sources & evidence

ORD record
ord-cf36f842c7b642b4bf8a85421e7cf8f2
Source dataset
uspto-grants-2012_03
Patent number
US08133911B2

Reaction notes

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