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Acetic Acid → HCID 178439937, Verbindung

HRID 931281
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 931281
C(O)(=O)C.[Cl:5][C:6]1[CH:7]=[N:8][N:9]([C:11]([CH3:18])([CH3:17])[C:12](=[NH:16])OCC)[CH:10]=1.[NH2:19][C:20]1[CH:21]=[CH:22][C:23]([N:27]2[CH2:32][CH2:31][CH2:30][C@@H:29]([C:33]([N:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)=[O:34])[CH2:28]2)=[N:24][C:25]=1N>C(O)C>[Cl:5][C:6]1[CH:7]=[N:8][N:9]([C:11]([C:12]2[NH:16][C:25]3=[N:24][C:23]([N:27]4[CH2:32][CH2:31][CH2:30][C@@H:29]([C:33]([N:35]5[CH2:39][CH2:38][CH2:37][CH2:36]5)=[O:34])[CH2:28]4)=[CH:22][CH:21]=[C:20]3[N:19]=2)([CH3:17])[CH3:18])[CH:10]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 89854052(R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanoneHCID 117966314Ethyl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanimidate2×

Produkt 1

HCID 178439937HCID 178439937, VerbindungAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

Acetic acid (2.9 mL, 48.58 mmol) and ethyl 2-(4-chloro-1H-pyrazol-1-yl)-2-methylpropanimidate (Intermediate 54) were added to a solution of (R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone in ethanol, prepared in the previous step. The reaction mixture was heated at reflux for 18 h. The mixture was concentrated and the residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude material was purified via column chromatography (100-200 mesh silica gel, 5% methanol in ethyl acetate) to afford the title compound (530 mg, 25% yield over 2 steps). 1H NMR (500 MHz, CDCl3) δ 1.53-1.65 (m, 1H) 1.74-2.00 (m, 7H) 2.10 (s, 6H) 2.58-2.70 (m, 1H) 2.88-2.93 (m, 1H) 3.01-3.09 (m, 1H) 3.40-3.50 (m, 3H) 3.55-3.63 (m, 1H) 4.22 (d, 1H) 4.43 (d, 1H) 6.63 (d, 1H) 7.57 (d, 2H) 7.79 (d, 1H) 10.08 (br s, 1H). MS (ES+APCI) (M+H) 442.2; LCMS retention time 2.216 min (Method N1).

Aufarbeitung

  1. customprepared in the previous step
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 18 h
  4. concentrationThe mixture was concentrated
  5. customthe residue was partitioned between ethyl acetate and water
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified via column chromatography (100-200 mesh silica gel, 5% methanol in ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2ca420089ec44c5ca888f269d9cc2387
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09296745B2

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