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

HRID 2172860Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2172860
[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

Komponenten

8

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f95d3b1a3b2045039ac902fb703ad4b9
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056865B2

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