Acetic Acid → HCID 178521015, Verbindung

HRID 931277

Reaktionsgleichung

Reaktionsgleichung von HRID 931277
[CH:1]1([C:4]2[CH:5]=[N:6][CH:7]=[C:8]([CH:14]=2)[C:9](=[NH:13])OCC)[CH2:3][CH2:2]1.C(O)(=O)C.C(N(CC)CC)C.Cl.Cl.[NH2:28][C:29]1[CH:30]=[CH:31][C:32]([N:36]2[CH2:41][CH2:40][CH2:39][C@@H:38]([C:42]([N:44]3[CH2:48][CH2:47][CH2:46][CH2:45]3)=[O:43])[CH2:37]2)=[N:33][C:34]=1N>C(O)C>[CH:1]1([C:4]2[CH:14]=[C:8]([C:9]3[NH:13][C:34]4=[N:33][C:32]([N:36]5[CH2:41][CH2:40][CH2:39][C@@H:38]([C:42]([N:44]6[CH2:48][CH2:47][CH2:46][CH2:45]6)=[O:43])[CH2:37]5)=[CH:31][CH:30]=[C:29]4[N:28]=3)[CH:7]=[N:6][CH:5]=2)[CH2:2][CH2:3]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 89853752Ethyl 5-cyclopropylnicotinimidateHCID 89854051(R)-(1-(5,6-Diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride

Produkt 1

HCID 178521015HCID 178521015, VerbindungAusbeute 5,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl 5-cyclopropylnicotinimidate (0.2 g, 1.04 mmol) in ethanol was added acetic acid (0.1 mL), triethylamine (0.1 mL) and a solution of (R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride salt (0.4 g, 1.1 mmol) in ethanol. The reaction mixture was heated at reflux for 24 h. The solvent was removed under reduced pressure and to the resulting residue was added a saturated aqueous solution of ammonium chloride. The mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The crude material was purified via preparative TLC to afford the title compound (0.025 g). 1H NMR (400 MHz, DMSO-d6) δ 0.85 (br s, 2H), 1.07 (d, 2H), 1.47-1.74 (m, 4H), 1.74-1.96 (m, 5H), 1.98-2.10 (m, 1H), 2.61 (br s, 2H), 2.92 (d, 2H), 3.41-3.59 (m, 2H), 4.33 (d, 1H), 4.39 (d, 1H), 6.86 (d, 1H), 7.81 (d, 1H), 8.00 (br s, 1H), 8.47 (br s, 1H), 9.05 (br s, 1H), 13.07 (br s, 1H). MS (ES+) (M+H) 417.36; LCMS retention time 3.03 min (Method S).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 24 h
  3. customThe solvent was removed under reduced pressure and to the resulting residue
  4. additionwas added a saturated aqueous solution of ammonium chloride
  5. extractionThe mixture was extracted with ethyl acetate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customThe crude material was purified via preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-18c3e61935e5430d967f3ea2d2868b9d
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296745B2

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