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

HRID 1068226ノート

反応式

HRID 1068226 の反応式
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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-284b0860f21640eb8a2aada83e60948d
出典データセット
uspto-grants-2001_06
特許番号
US06248755B1

反応ノート

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