1,2-Dichloroethane → HCID 16124925, compound

HRID 1945417Notes

Reaction equation

HRID 1945417 reaction equation
[C:1]12([C:11]3[CH:30]=[CH:29][C:14]([O:15][CH2:16][C:17]([NH:19][C:20]4[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=4)[C:23](O)=[O:24])=[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.[CH:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][C:32]=1[NH2:41].CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(OCC)(=O)C>[C:1]12([C:11]3[CH:30]=[CH:29][C:14]([O:15][CH2:16][C:17]([NH:19][C:20]4[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=4)[C:23]([NH:41][C:32]4[CH:33]=[CH:34][C:35]5[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=5)[CH:31]=4)=[O:24])=[O:18])=[CH:13][CH:12]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 70572-NaphthylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5124065HCID 5124065, compound

Product 1

HCID 16124925HCID 16124925, compoundYield 61.53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-benzoic acid (20 mg, 0.049 mmol), 2-naphthylamine (10.59 mg, 0.073 mmol) and DIPEA (9.56 mg, 0.073 mmol) in DMF 1 mL was added EDC (14.18 mg, 0.073 mmol) and HOBt (9.99 mg, 0.073 mmol) at room temperature and continued string for 16 h at room temperature. Reaction mixture was diluted with ethyl acetate and sequentially washed with aqueous sodium bicarbonate, brine and water, and dried over MgSO4. The solvent was filtered and evaporated under reduced pressure to afford a crude solid, which was purified by column chromatography on silica gel (n-Hexane:EtoAC=1:9˜4:6) to give 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-N-naphtalene-2-yl-benzamide as a colorless crystals (16 mg, 61.53% yield).

Workup

  1. customfor 16 h
  2. customat room temperature
  3. customReaction mixture
  4. washsequentially washed with aqueous sodium bicarbonate, brine and water
  5. dry with materialdried over MgSO4
  6. filtrationThe solvent was filtered
  7. customevaporated under reduced pressure
  8. customto afford a crude solid, which
  9. customwas purified by column chromatography on silica gel (n-Hexane:EtoAC=1:9˜4:6)

Sources & evidence

ORD record
ord-1a7311d7378d4d7288edb405f13b653d
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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