Acetic Acid → HCID 11693007, compound

HRID 1394365Notes

Reaction equation

HRID 1394365 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([N:12]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=2)[CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[F:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C1COCC1>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([C:10]([N:12]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=2)[CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([NH:36][C:35]3[CH:37]=[CH:38][C:32]([F:31])=[CH:33][CH:34]=3)[CH2:18][CH2:17]2)=[O:11])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 97314-FluoroanilineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 11518124HCID 11518124, compound

Product 1

HCID 11693007HCID 11693007, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound obtained in Example 208 (1000 mg, 2.2 mmol) and 4-fluoroaniline (269 mg, 2.4 mmol) in THF (3 mL) were added acetic acid (0.126 mL, 2.2 mmol) and sodium triacetoxyborohydride (699 mg, 3.3 mmol) under ice cooling, and the mixture was stirred at room temperature for 20 hours. To the reaction mixture was added saturated aqueous solution of sodium hydrogen carbonate (100 mL). The mixture was stirred at room temperature for 2 hours and extracted with ethyl acetate (100 mL×2). The organic layer was washed with saturated sodium chloride solution (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was subjected to flash column chromatography (silica gel 20 g, ethyl acetate/methanol=1/0 to 9/1 to 4/1), and the desired fraction was concentrated under reduced pressure to give the titled compound (695 mg, 1.3 mmol, Yield 58%) as a pale purple amorphous substance.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. extractionextracted with ethyl acetate (100 mL×2)
  3. washThe organic layer was washed with saturated sodium chloride solution (100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. concentrationthe desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c6807009e6c5431a8813f4666fb27f4c
Source dataset
uspto-grants-2008_03
Patent number
US07348324B2

Reaction notes

Loading…