Trifluoroacetic acid → HCID 57932938, compound

HRID 1432674Notes

Reaction equation

HRID 1432674 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:21][C:20]([C:22]4(O)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[N:19][C:18]=3[CH3:29])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[O:25]1[CH2:24][CH:23]=[C:22]([C:20]2[S:21][C:17]([C:13]3[N:8]4[N:9]=[C:10]([CH3:12])[CH:11]=[C:6]([CH:3]([CH2:1][CH3:2])[CH2:4][CH3:5])[C:7]4=[N:15][C:14]=3[CH3:16])=[C:18]([CH3:29])[N:19]=2)[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68840954HCID 68840954, compound

Product 1

HCID 57932938HCID 57932938, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

150 mg of 4-{5-[8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-4-methyl-thiazol-2-yl}-tetrahydro-pyran-4-ol (0.36 mmol) is dissolved in 5 ml of CH2Cl2 and 112 mg of triethylsilane (0.96 mmol) and 717 mg of trifluoroacetic acid (6.3 mmol) are added. The reaction mixture is stirred at room temperature for 1 h. The reaction mixture is stirred under reflux for 1 h and cooled down to room temperature. The solvent is removed in vacuo. The crude product is applied onto a silica-gel chromatography column (Hexane:AcOEt:2 M NH3 in MeOH=10:3:1) to give 64 mg of the title compound. Yield 45%. mass spectrum (m/e): 397 (M+1). 6.94 (s, 1H), 6.71 (s, 1H), 4.41 (d, J=2.6 Hz, 2H), 3.98 (t, J=5.3 Hz, 2H), 3.43 (m, 1H), 2.62 (s, 3H), 2.75 (m, 2H), 2.56 (s, 3H), 2.37 (s, 3H), 1.86 (m, 4H), 0.92 (t, J=8.2 Hz, 6H).

Workup

  1. stirringThe reaction mixture is stirred
  2. temperatureunder reflux for 1 h
  3. temperaturecooled down to room temperature
  4. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-ff37e9bf805d40758f5a394bd0f45308
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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