1,2-Dichloroethane → HCID 16124990, compound

HRID 1945418Notes

Reaction equation

HRID 1945418 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]([OH:25])=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.[NH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1.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:12]=[CH:13][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:31][CH2:32][CH2:33][C:34]4[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=4)=[O:25])=[O:18])=[CH:29][CH:30]=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 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 832754-PyridineethanamineHCID 5124065HCID 5124065, compound

Product 1

HCID 16124990HCID 16124990, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-benzoic acid (50 mg, 0.123 mmol), 4-(2-aminoethyl)pyridine (22.59 mg, 0.184 mmol) and DIPEA (23.90 mg, 0.184 mmol) in DMF 1 mL was added EDC (35.45 mg, 0.184 mmol) and HOBt (24.99 mg, 0.184 mmol) at room temperature and continued stirring 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=1:5) to give 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-N-(2-pyridine-4-yl-ethyl)benzamide as a colorless crystal (25 mg, 40% yield).

Workup

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

Sources & evidence

ORD record
ord-b7f83bf7a8024c2dbdf8e6165a426a44
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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