Water → HCID 66692526, compound

HRID 710561Notes

Reaction equation

HRID 710561 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].ClC1C=C(C=CC=1OC)C[N:23]1[CH2:28][CH2:27][CH:26]([NH:29][C:30]([N:32]2[CH2:37][CH2:36][C:35](=[CH:38][C:39]3[CH:44]=[C:43]([F:45])[CH:42]=[CH:41][C:40]=3[F:46])[CH2:34][CH2:33]2)=[O:31])[CH2:25][CH2:24]1.O>CN(C=O)C>[F:46][C:40]1[CH:41]=[CH:42][C:43]([F:45])=[CH:44][C:39]=1[CH:38]=[C:35]1[CH2:36][CH2:37][N:32]([C:30]([NH:29][CH:26]2[CH2:25][CH2:24][N:23]([C:7]3[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:11])=[CH:5][CH:6]=3)[CH2:28][CH2:27]2)=[O:31])[CH2:33][CH2:34]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67878Methyl 4-fluorobenzoateHCID 66691939HCID 66691939, compound

Product 1

HCID 66692526HCID 66692526, compoundYield 4.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

4-Fluorobenzoic acid methyl ester (125 mg, 0.807 mmol) was dissolved in DMF (3.0 mL), and potassium carbonate (150 mg, 1.08 mmol) and the compound (200 mg, 0.538 mmol) obtained in Example 36 (1) were added thereto, followed by stirring overnight while heating at 120° C. After the reaction mixture was cooled to room temperature, water was added thereto. After extraction with chloroform, the extract was washed with water and a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the residue obtained by evaporation under reduced pressure was purified using medium pressure silica gel flash column chromatography (methanol:chloroform=1:100), thereby giving the title compound (11.0 mg, 4%) as a white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionAfter extraction with chloroform
  3. washthe extract was washed with water
  4. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  5. filtrationThe desiccant was filtered off
  6. customthe residue obtained by evaporation under reduced pressure
  7. customwas purified

Sources & evidence

ORD record
ord-ec43ad2ca7a14f61b0dc493f4f2dfd9f
Source dataset
uspto-grants-2015_11
Patent number
US09181183B2

Reaction notes

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