1,2-Dichloroethane → 1-(t-Butoxycarbonyl)-4-(2-(2-pyridinyl)hydrazino)carbonyl-piperidine

HRID 1068226노트

반응식

HRID 1068226 반응식
Cl.Cl.[NH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)[NH2:4].[C:11]([N:18]1[CH2:23][CH2:22][CH:21]([C:24](O)=[O:25])[CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[C:14]([O:13][C:11]([N:18]1[CH2:23][CH2:22][CH:21]([C:24]([NH:4][NH:3][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=2)=[O:25])[CH2:20][CH2:19]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 64543982-Pyridone hydrazone dihydrochloride

생성물 1

HCID 211930971-(t-Butoxycarbonyl)-4-(2-(2-pyridinyl)hydrazino)carbonyl-piperidine수율 75.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of 2-hydrazinopyridine dihydrochloride (2.49 g, 13.7 mmol) and 1-Boc-piperidine-4-carboxylic acid (3.14 g, 13.7 mmol) in 30 mL of CH2Cl2 was added DIPEA (5.96 mL) followed by HOBT (2.22 g, 16.4 mmol) and EDC (3.93 g, 20.5 mmol) at rt. After stirring at rt for 18 h, the reaction mixture was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2 (3×). Combined organic phase was washed with brine and dried over anhydrous MgSO4. Concentration under reduced pressure afforded the title compound (3.3 g) as a white solid. 1H NMR (500 MHz, CDCl3): δ 1.47 (s, 9H), 1.68-1.76 (m, 2H), 1.86-1.88 (m, 2H), 2.44 (m, 1H), 2.70-2.90 (br, 2H), 4.15-4.22 (br, 2H), 6.71 (d, J=8.5 Hz, 1H), 6.81 (t, J=6.4 Hz, 1H), 7.56 (m, 1H), 8.11 (d, J=5.0 Hz, 1H), 8.20˜8.55 (br s, 1H).

후처리

  1. customthe reaction mixture was partitioned between CH2Cl2 and water
  2. extractionThe aqueous layer was extracted with CH2Cl2 (3×)
  3. washCombined organic phase was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationConcentration under reduced pressure

출처 및 근거

ORD 기록
ord-284b0860f21640eb8a2aada83e60948d
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248755B1

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