HCID 54438385, compound → 4-(fluoro(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)-N-(6-methylpyridin-3-yl)piperidine-1-carboxamide

HRID 1666491

Reaction equation

HRID 1666491 reaction equation
[F:1][C:2](=[C:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=1.[CH3:26][C:27]1[N:32]=[CH:31][C:30]([NH:33][C:34](=O)[O:35]C2C=CC=CC=2)=[CH:29][CH:28]=1>CS(C)=O.C(N(CC)CC)C.O>[F:1][C:2]([C:3]1[CH:19]=[CH:18][CH:17]=[C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:15])([F:16])[F:14])=[CH:9][N:8]=2)[CH:4]=1)=[C:20]1[CH2:25][CH2:24][N:23]([C:34]([NH:33][C:30]2[CH:31]=[N:32][C:27]([CH3:26])=[CH:28][CH:29]=2)=[O:35])[CH2:22][CH2:21]1

Participants

6

Reactant 2

HCID 54438385HCID 54438385, compoundHCID 668762662-(3-(Fluoro(piperidin-4-ylidene)methyl)phenoxy)-5-(trifluoromethyl)pyridine

Product 1

HCID 668761254-(fluoro(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)-N-(6-methylpyridin-3-yl)piperidine-1-carboxamideYield 59.3%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(3-(fluoro(piperidin-4-ylidene)methyl)phenoxy)-5-(trifluoromethyl)pyridine (110 mg, 0.312 mmol) and phenyl 6-methylpyridin-3-ylcarbamate (71.2 mg, 0.312 mmol) in DMSO (5 mL) under a N2 atmosphere was added 5 drops of triethyl amine and the reaction mixture was stirred for 12 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water several times to remove the excess DMSO. The title compound was crystallized from hexane and diethyl ether to give the pure title compound (90 mg). 1H NMR (500 MHz, CDCl3): δ 2.5 (brs, 2H), 2.6 (brs, 2H), 2.8 (s, 3H), 3.7 (brs, 2H), 3.8 (brs, 2H), 7.0 (d, 1H, J=7.5 Hz), 7.1-7.3 (m, 3H), 7.4 (m, 2H), 7.9 (d, 1H, J=7.5 Hz), 8.4 (s, 1H), 9.0 (d, 1H, J=8.5 Hz), 9.4 (s, 1H), 9.8 (s, 1H); 13C NMR (125 MHz, CDCl3): 22.6, 25.6, 27.8, 44.2, 44.4, 53.4, 111.6, 114.1, 114.3, 121.4, 122.0, 123.8, 125.3, 129.7, 130.0, 133.8, 134.7, 136.9, 138.7, 145.4, 151.8, 153.0, 154.6, 165.4; m/z (487.4 M+ H+); HPLC: 98.9%; MP: 158-160° C.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water several times
  3. customto remove the excess DMSO
  4. customThe title compound was crystallized from hexane and diethyl ether

Sources & evidence

ORD record
ord-97478792f5ae4ec4886a9ff577f71e1a
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Linked notes

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