Water → HCID 53652917, compound

HRID 1598916Notes

Reaction equation

HRID 1598916 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[C:14]([O:18][C:19](=[O:46])[CH2:20][N:21]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[Sn](C)(C)C)[C:22](=[O:35])[CH2:23][NH:24][C:25]([NH:27][C:28]1[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=1)=[O:26])([CH3:17])([CH3:16])[CH3:15].O>C1(C)C=CC=CC=1>[C:14]([O:18][C:19](=[O:46])[CH2:20][N:21]([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:41]=1[C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=1)[C:22](=[O:35])[CH2:23][NH:24][C:25]([NH:27][C:28]1[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=1)=[O:26])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 18930557HCID 18930557, compound2×

Product 1

HCID 53652917HCID 53652917, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-trifluoromethylbenzoyl chloride (53 μl, 0.36 mmol) in toluene (4 ml) is added dichlorobisacetonitrile palladium (12.5 mg, 0.036 mmol) at room temperature. Then, tert-butyl((2-trimethylstannylphenyl)-(2-(3-m-tolylureido)acetyl)amino)acetate (compound 25) (200 mg, 0.36 mmol) is added, and the mixture is stirred at 50° C. for 20 minutes. After addition of dichlorobisacetonitrile palladium (6.2 mg, 0.018 mmol), stirring is confinated for additional 10 minutes. To the reaction solution is added ice-cooled water. After stirring, the aqueous layer is extracted twice with ethyl acetate. The organic layer is washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The residue is purified by subjecting to silica gel column chromatography to obtain the objective compound 26a (93 mg). Yield 46%.

Workup

  1. stirringstirring
  2. waitis confinated for additional 10 minutes
  3. additionTo the reaction solution is added ice-
  4. stirringAfter stirring
  5. extractionthe aqueous layer is extracted twice with ethyl acetate
  6. washThe organic layer is washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue is purified

Sources & evidence

ORD record
ord-3d1677c5f5274ada9252401e0233f653
Source dataset
uspto-grants-1998_04
Patent number
US05739162

Reaction notes

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