Potassium Carbonate → HCID 24769552, compound

HRID 1641432Notes

Reaction equation

HRID 1641432 reaction equation
[F:1][CH:2]([F:16])[C:3]1[CH:4]=[N:5][N:6]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[C:7]=1[CH3:8].Cl.Cl[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:16][CH:2]([F:1])[C:3]1[CH:4]=[N:5][N:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:11][CH:10]=2)[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 59660698HCID 59660698, compound

Product 1

HCID 24769552HCID 24769552, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(4-Difluoromethyl-5-methyl-pyrazol-1-yl)-phenol (30 mg, 0.134 mmol), 1-(2-chloroethyl)piperidine hydrochloride (50 mg, 0.27 mmol), K2CO3 (55 mg, 0.4 mmol), in DMF (1 mL) was stirred at 90° C. for 18 h. After the reaction mixture was quenched with water, the reaction mixture was extracted with CH2Cl2, washed 10% NaOH, and brine, dried over Na2SO4. After concentrated in vacuo, the residue was purified by a column chromatography on silica gel eluting with 20% ethyl acetate/hexane to yield the title compound (25 mg, 56%); 1H NMR (400 MHz, CDCl3) 7.70 (br s, 1H), 7.30 (d, J=13.2 Hz, 1H), 7.00 (d, J=13.2 Hz, 2H), 6.71 (t, J=96, 52 Hz, 1H), 4.16 (t, J=12, 6 Hz, 2H), 2.65 (t, J=12, 6 Hz, 2H), 2.53 (br, 4H), 2.34 (s, 3H), 1.61-1.47 (m, 6H); LC/MS (ESI) m/z: 336 (M+1, 100), 97%.

Workup

  1. customAfter the reaction mixture was quenched with water
  2. extractionthe reaction mixture was extracted with CH2Cl2
  3. washwashed 10% NaOH, and brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentrated in vacuo
  6. customthe residue was purified by a column chromatography on silica gel eluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-bdcf3bfb077449389a722cbd253ddba0
Source dataset
uspto-grants-2012_02
Patent number
US08115005B2

Reaction notes

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