Potassium Carbonate → HCID 21865295, compound

HRID 857685Notes

Reaction equation

HRID 857685 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.C([O-])([O-])=O.[K+].[K+].[N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:27][C:28]3[N:33]=[CH:32][N:31]=[C:30]([C:34]4[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][C:35]=4[OH:44])[CH:29]=3)[CH:25]=2)[CH:20]=[CH:19][CH:18]=1.[H-].[Na+]>CN(C=O)C.O>[N:5]1([CH2:4][CH2:3][O:44][C:35]2[CH:36]=[C:37]([C:40]([F:42])([F:43])[F:41])[CH:38]=[CH:39][C:34]=2[C:30]2[N:31]=[CH:32][N:33]=[C:28]([O:27][C:24]3[CH:25]=[C:26]4[C:21]([CH:20]=[CH:19][CH:18]=[N:17]4)=[CH:22][CH:23]=3)[CH:29]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 135516888HCID 135516888, compound

Product 1

HCID 21865295HCID 21865295, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of 4-(2-chloroethyl)morpholine hydrochloride (58 mg, 0.31 mmol, Aldrich) in DMF (1.0 mL) was stirred at room temperature and treated with K2CO3 (86 mg, 0.62 mmol). After stirring for 5 min, the resulting solution was added to a mixture of 2-[6-(quinolin-7-yloxy)-pyrimidin-4-yl]-5-trifluoromethylphenol, (Example 191), (100 mg, 0.26 mmol) and NaH (13 mg, 0.52 mmol, 95%, Aldrich) in DMF (2.0 mL) at room temperature. The reaction mixture was stirred at room temperature for 1 h and then heated at 70° C. for 20 h. The resulting mixture was allowed to cool to room temperature and diluted with water. The organic phase was separated, and the aqueous phase was extracted with CH2Cl2. The combined extracts were washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuum. Purification by silica gel chromatography (gradient 0% to 4.0% MeOH/CH2Cl2) afforded the title compound as a white solid. MP: 132–133° C. MS (ESI, pos. ion) m/z: 497 (M+1).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 h
  2. temperatureto cool to room temperature
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with CH2Cl2
  5. washThe combined extracts were washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuum
  9. customPurification by silica gel chromatography (gradient 0% to 4.0% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-0ccc1789e15942338b39756b8c7cf37c
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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