1,2-Dichloroethane → HCID 24812093, compound

HRID 1945430Notes

Reaction equation

HRID 1945430 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.N[C:23]1[C:24]([CH3:29])=[CH:25][CH:26]=[N:27][CH:28]=1.CC[N:32](C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[C:1]12([C:11]3[CH:12]=[CH:13][C:14]([O:15][CH2:16][C:17]([NH:32][C:26]4[CH:25]=[C:24]([CH3:29])[CH:23]=[CH:28][N:27]=4)=[O:18])=[CH:20][CH:21]=3)[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1379353-Amino-4-picolineHCID 625381PMID26882240-Compound-8

Product 1

HCID 24812093HCID 24812093, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To solution of (4-adamantan-1-yl-phenoxy)-acetic acid (50 mg, 0.17 mmol), 5-amino-4-picoline (28.32 mg, 0.26 mmol) and DIPEA (33.85 mg, 0.26 mmol) in DMF 1 mL was added EDC (50.2 mg, 0.26 mmol) and HOBt (35.39 mg, 0.26 mmol) at room temperature. Reaction mixture was stirred at room temperature. Resulting mixture poured onto ice cold water, was extracted with ethyl acetate, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (EtoAC:Hexane=1:9˜2:8) to give 2-(4-adamantan-1-yl-phenoxy)-N-(4-methyl-pyridine-2-yl)-acetamide as a colorless solid (0.033 g, 50% yield).

Workup

  1. customReaction mixture
  2. customResulting mixture
  3. additionpoured onto ice cold water
  4. extractionwas extracted with ethyl acetate
  5. washsequentially washed with aqueous sodium bicarbonate, brine and water
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash silica gel column chromatography (EtoAC:Hexane=1:9˜2:8)

Sources & evidence

ORD record
ord-0d170a191e584879816e80886eb03c51
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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