4-Methylmorpholine → 1-(4-(5'-Chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)piperazin-1-yl)-3-(methylsulfonyl)propan-1-one

HRID 2172860노트

반응식

HRID 2172860 반응식
[Cl:1][C:2]1[C:3]([C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][N:15]=2)=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C.[CH3:50][S:51]([CH2:54][CH2:55][C:56](O)=[O:57])(=[O:53])=[O:52]>C(Cl)Cl.C(Cl)Cl.CO>[Cl:1][C:2]1[C:3]([C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][N:15]=2)=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:56](=[O:57])[CH2:55][CH2:54][S:51]([CH3:50])(=[O:53])=[O:52])[CH2:10][CH2:9]2)=[N:6][CH:7]=1

참가 물질

8

반응물 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1203083-(Methylsulfonyl)propanoic acidHCID 675095955'-Chloro-3,5-dimethyl-2'-(piperazin-1-yl)-2,4'-bipyridine

생성물 1

HCID 569562401-(4-(5'-Chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)piperazin-1-yl)-3-(methylsulfonyl)propan-1-one수율 90%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21226129Dichloromethane methanol용매

실험 절차

To a solution of 5′-chloro-3,5-dimethyl-2′-(piperazin-1-yl)-2,4′-bipyridine (2.3 g, 15.1 mmol) and HOBT (2.55 g, 18.9 mmol) in CH2Cl2 (60 mL) was added NMM (5.67 g, 56.7). After stirring for 30 min at room temperature, EDCI (3.63 g, 18.9 mmol) and 3-(methylsulfonyl)propanoic acid (3.9 g, 12.6 mmol) were added and the mixture was stirred at 30° C. for 18 hours. TLC (CH2Cl2/MeOH=10:1) showed the starting material was consumed completely. After removal of the solvent in vacuo, the residue was dissolved in CH2Cl2 (180 mL), washed with saturated aq. NaHCO3 (40 mL), saturate aq. NH4Cl (40 mL) and brine (40 mL). The resulting material was dried over Na2SO4 and concentrated in vacuo to give title compound (4.8 g, 90%) as white solid. 1H NMR (400 MHz, CDCl3): δ 8.28 (s, 1H), 8.15 (s, 1H), 7.36 (s, 1H), 6.53 (s, 1H), 3.69-3.66 (m, 2H), 3.58-5.53 (m, 4H), 3.48-3.46 (m, 2H), 3.41-3.37 (m, 2H), 2.94 (s, 3H) 2.89-2.86 (m, 2H), 2.31 (s, 3H), 2.10 (s, 3H); m/z for C20H25ClN4O3S 437.3 (M+H)+.

후처리

  1. stirringthe mixture was stirred at 30° C. for 18 hours
  2. customwas consumed completely
  3. customAfter removal of the solvent in vacuo
  4. dissolutionthe residue was dissolved in CH2Cl2 (180 mL)
  5. washwashed with saturated aq. NaHCO3 (40 mL)
  6. concentrationsaturate aq. NH4Cl (40 mL) and brine (40 mL)
  7. dry with materialThe resulting material was dried over Na2SO4
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f95d3b1a3b2045039ac902fb703ad4b9
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056865B2

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