1,2-Dichloroethane → N-[(1R)-1-(5-fluoro-2-pyridinyl)ethyl]-3-(5-methyl-2-pyridinyl)-5-vinylbenzamide

HRID 1257541노트

반응식

HRID 1257541 반응식
[Cl-].[Na+].[Na+].[Na+].[Cl-].[Cl-].[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:15]=[C:16]([CH:20]=[C:21]([CH:23]=[CH2:24])[CH:22]=2)[C:17]([OH:19])=O)=[N:12][CH:13]=1.Cl.[F:26][C:27]1[CH:28]=[CH:29][C:30]([C@H:33]([NH2:35])[CH3:34])=[N:31][CH:32]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[F:26][C:27]1[CH:28]=[CH:29][C:30]([C@H:33]([NH:35][C:17](=[O:19])[C:16]2[CH:20]=[C:21]([CH:23]=[CH2:24])[CH:22]=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([CH3:7])=[CH:13][N:12]=3)[CH:15]=2)[CH3:34])=[N:31][CH:32]=1

참가 물질

9

반응물 7

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 23615961Tri-sodium chlorideHCID 66690953(1R)-1-(5-fluoropyridin-2-yl)ethan-1-amine hydrochlorideHCID 668957363-(5-Methyl-2-pyridinyl)-5-vinylbenzoic acid

생성물 1

HCID 66895503N-[(1R)-1-(5-fluoro-2-pyridinyl)ethyl]-3-(5-methyl-2-pyridinyl)-5-vinylbenzamide수율 52.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of tri-sodium chloride adduct of 3-(5-methyl-2-pyridinyl)-5-vinylbenzoic acid (2.5 g, 6.0 mmol) in N,N-dimethylformamide (20 mL) were added (1R)-1-(5-Fluoropyridin-2-yl)ethanamine hydrochloride (1.60 g, 7.5 mmol), EDC (2.02 g, 10.5 mmol), HOAT (0.25 g, 1.8 mmol) and triethylamine (3.36 mL, 24 mmol). The reaction mixture was stirred at ambient temperature for 18 h. Saturated aqueous sodium bicarbonate was added. The mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→100% ethyl acetate) gave the title compound (1.14 g). MS 362.1 (M+1).

후처리

  1. extractionThe mixture was extracted with dichloromethane (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (100% hexanes→100% ethyl acetate)

출처 및 근거

ORD 기록
ord-d514aa66fb404d55a055e81d3ee2edb5
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461185B2

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