N-(2-Aminoethyl)piperidine → (4-Isopropyl-piperazin-1-yl)-[6-(2-piperidin-1-yl-ethylamino)-pyridin-3-yl]-methanone

HRID 30465

반응식

HRID 30465 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH:16]([CH3:18])[CH3:17])[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[NH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C(O)CCC>[NH3:7].[CH:16]([N:13]1[CH2:14][CH2:15][N:10]([C:8]([C:5]2[CH:6]=[N:7][C:2]([NH:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:3][CH:4]=2)=[O:9])[CH2:11][CH2:12]1)([CH3:18])[CH3:17]

참가 물질

5

반응물 2

HCID 33944N-(2-Aminoethyl)piperidineHCID 43420904(6-Chloro-pyridin-3-yl)-(4-isopropyl-piperazin-1-yl)-methanone

생성물 2

HCID 222Ammonia수율 2%HCID 11710212(4-Isopropyl-piperazin-1-yl)-[6-(2-piperidin-1-yl-ethylamino)-pyridin-3-yl]-methanone수율 37.1%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

A solution of (6-chloro-pyridin-3-yl)-(4-isopropyl-piperazin-1-yl)-methanone (0.20 g, 0.75 mmol) and 1-(2-aminoethyl)-piperidine (0.16 mL, 1.13 mmol) in 1-butanol (10 mL) was heated at reflux temperature. After 18 h the reaction was concentrated, treated with 1 N aq. NaHCO3 (25 mL), and extracted with DCM (3×25 mL). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the residue (SiO2: 2-5% 2 M NH3 in MeOH/DCM) gave the title compound as an oil (0.050 g, 20%). MS (ESI): exact mass calcd. for C20H33N5O, 359.3; m/z found, 360.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.20 (d, J=1.8, 1H), 7.54 (dd, J=8.6, 2.3, 1H), 6.40 (d, J=9.0, 1H), 5.49 (br s, 1H), 3.65 (br s, 4H), 3.39-3.35 (m, 2H), 2.74-2.70 (m, 1H), 2.59-2.57 (m, 2H), 2.53 (br s, 4H), 2.42 (br s, 4H), 1.62-1.56 (m, 4H), 1.46-1.45 (m, 2H), 1.04 (d, 6.5, 6H).

후처리

  1. temperatureat reflux temperature
  2. concentrationAfter 18 h the reaction was concentrated
  3. additiontreated with 1 N aq. NaHCO3 (25 mL)
  4. extractionextracted with DCM (3×25 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ef3cb752837e487893a5fc6d81306e67
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423147B2

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