Water → HCID 24965849, compound

HRID 1666522Notes

Reaction equation

HRID 1666522 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5](=[CH:8][C:9]2[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=2)[O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=2)[CH2:4][CH2:3]1.[C:26]([C:29]1[S:33][C:32]([NH:34][C:35](=O)[O:36]C2C=CC=CC=2)=[N:31][C:30]=1[CH3:44])(=[O:28])[CH3:27].C(N(CC)CC)C.O>CS(C)=O>[C:26]([C:29]1[S:33][C:32]([NH:34][C:35]([N:2]2[CH2:7][CH2:6][C:5](=[CH:8][C:9]3[CH:25]=[CH:24][CH:23]=[C:11]([O:12][C:13]4[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:15][N:14]=4)[CH:10]=3)[CH2:4][CH2:3]2)=[O:36])=[N:31][C:30]=1[CH3:44])(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 22259036Phenyl (5-acetyl-4-methyl-1,3-thiazol-2-yl)carbamateHCID 668761612-(3-(Piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine hydrochloride

Product 1

HCID 24965849HCID 24965849, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-(3-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine hydrochloride (0.100 g; Example 1a, Step 5), phenyl 5-acetyl-4-methylthiazol-2-ylcarbamate (0.089 g, 1.2 equiv), and triethylamine (0.045 mL, 1.2 equiv) in dimethyl sulfoxide (1 mL, 0.3 M) was heated to 65° C. for 2 h. The reaction was cooled to room temperature. Water was added and then the solution was extracted with ethyl acetate (2×). The organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was purified on a 12 g silica gel column using 10-30% ethyl acetate/dichloromethane over 20 minutes as the eluent to give the title compound as a light yellow foam. 0.065 g, 47% yield. 1H NMR (400 MHz, CDCl3) δ ppm 2.44-2.54 (5H, m), 2.61 (2H, t, J=5.7 Hz), 2.66 (3H, s), 3.63 (2H, t, J=5.8 Hz), 3.73 (2H, t, J=5.9 Hz), 6.42 (1H, s), 6.92-7.04 (3H, m), 7.07 (1H, d, J=7.8 Hz), 7.38 (1H, t, J=8.0 Hz), 7.89 (1H, dd, J=8.6, 2.7 Hz), 8.43 (1H, s).

Workup

  1. extractionthe solution was extracted with ethyl acetate (2×)
  2. dry with materialThe organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on a 12 g silica gel column
  6. customover 20 minutes

Sources & evidence

ORD record
ord-76ed2701971b49eeacaa16fb41a75e14
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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