Potassium Carbonate → HCID 11497258, compound

HRID 2422630Notes

Reaction equation

HRID 2422630 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:30])[N:7]([CH3:29])[C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:14][C:13]=3[OH:28])=[N:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].S(C1C=CC(C)=CC=1)(O[CH2:41][CH2:42][F:43])(=O)=O>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:30])[N:7]([CH3:29])[C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:14][C:13]=3[O:28][CH2:41][CH2:42][F:43])=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2560192-Fluoroethyl p-ToluenesulfonateHCID 136343911HCID 136343911, compound

Product 1

HCID 11497258HCID 11497258, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-Bromo-2-[2-hydroxy-4-(3-piperidin-1-ylpropoxy)phenyl]-3-methylquinazolin-4(3H)-one (9.5 mg, 0.020 mmol) and potassium carbonate (8.3 mg, 0.06 mmol) were stirred in DMF (0.5 mL) at room temperature, and 2-fluoroethyl tosylate (6.6 mg, 0.03 mmol) was dropwise added thereto and stirred at room temperature for 3 hours. The reaction solution was diluted with ethyl acetate, washed with water and saturated saline water, and the organic layer was dried with magnesium sulfate. The solvent was evaporated off, and the residue was purified through silica gel thin-layer chromatography (chloroform/methanol=9/1) to obtain the intended compound (4.5 mg, 47%) as a milky white solid.

Workup

  1. washwashed with water and saturated saline water
  2. dry with materialthe organic layer was dried with magnesium sulfate
  3. customThe solvent was evaporated off
  4. customthe residue was purified through silica gel thin-layer chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-4e0f8b33edb24f31b54694a4e5274fb8
Source dataset
uspto-grants-2011_06
Patent number
US07960394B2

Reaction notes

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