1,2-Dichloroethane → HCID 24811213, compound

HRID 1945397Notes

Reaction equation

HRID 1945397 reaction equation
[C:1]12([C:11]3[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17](O)=[O:18])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[F:22][C:23]([F:32])([F:31])[C:24]1[CH:25]=[C:26]([NH2:30])[CH:27]=[CH:28][CH:29]=1.CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[C:1]12([C:11]3[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17]([NH:30][C:26]4[CH:27]=[CH:28][CH:29]=[C:24]([C:23]([F:31])([F:32])[F:22])[CH:25]=4)=[O:18])=[CH:13][CH:12]=3)[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 73753-(Trifluoromethyl)anilineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 625381PMID26882240-Compound-8

Product 1

HCID 24811213HCID 24811213, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-adamantan-1-yl-phenoxy)-acetic acid (50 mg, 0.17 mmol), 3-trifluoromethyl-phenylamine (42 mg, 0.26 mmol) and DIPEA (33.85 mg, 0.26 mmol) in DMF (2 mL) was added EDC (50.2 mg, 0.26 mmol) and HOBt (35.39 mg, 0.26 mmol) at room temperature. The reaction mix was stirred at room temperature until completion and then poured into water (100 mL). The resulting solid was extracted with ethyl acetate, washed with brine, aqueous sodium bicarbonate and water, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The resulting crude product was purified by flash chromatography on silica gel (EtOAc: hexanes=1:9 to 2:8) to afford of 2-(4-adamantan-1-yl-phenoxy)-N-(3-trifluoromethyl-phenyl)acetamide as a colorless solid (0.061 g, 81% yield).

Workup

  1. additionThe reaction mix
  2. extractionThe resulting solid was extracted with ethyl acetate
  3. washwashed with brine, aqueous sodium bicarbonate and water
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting crude product was purified by flash chromatography on silica gel (EtOAc: hexanes=1:9 to 2:8)

Sources & evidence

ORD record
ord-e8a64657b9bf4dd6ab162501670064bd
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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