Diisopropylethylamine → N-Methoxy-2-pyridin-2-yl-3,4-dihydroquinoline-1(2H)-carboxamide

HRID 589097

반응식

HRID 589097 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8]1.[CH3:17][O:18][NH:19][C:20](=O)[O:21]C1C=CC([N+]([O-])=O)=CC=1.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[CH3:17][O:18][NH:19][C:20]([N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:15][CH2:16][CH:7]1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:21]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 115647354-Nitrophenyl methoxycarbamateHCID 904098222-Pyridin-2-yl-1,2,3,4-tetrahydroquinoline

생성물 1

HCID 90408927N-Methoxy-2-pyridin-2-yl-3,4-dihydroquinoline-1(2H)-carboxamide수율 95%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A solution of 2-pyridin-2-yl-1,2,3,4-tetrahydroquinoline (0.723 g, 3.44 mmol) in methylene chloride (10.3 mL) was treated with 4-nitrophenyl methoxycarbamate (0.948 g, 4.47 mmol) (Org. Process Res. Dev. 2012, 16, 109-116) followed by the dropwise addition of N,N-diisopropylethylamine (1.20 mL, 6.88 mmol), and the resulting mixture was stirred at room temperature for 1.5 h. The reaction mixture was then poured over water (25 mL) and saturated sodium bicarbonate (25 mL) and extracted with dichloromethane (2×50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to give a crude oily solid. Purification by flash column chromatography (100% hexanes to 20% ethyl acetate/hexanes [the ethyl acetate contained 5% methanol]) gave the desired product (0.923 g, 95%) as a racemic mixture. LCMS calculated for C16H18N3O2 (M+H)+: m/z=284.1. found: 284.0.

후처리

  1. extractionextracted with dichloromethane (2×50 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude oily solid
  6. customPurification by flash column chromatography (100% hexanes to 20% ethyl acetate/hexanes [the ethyl acetate

출처 및 근거

ORD 기록
ord-ab994f55efbd452aa72be3d56fa76a88
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227985B2

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