Acetic Acid → HCID 178464471, Verbindung

HRID 931278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 931278
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]([N:17]([CH2:19][CH3:20])[CH3:18])=[O:16])[CH2:10]2)=[N:6][C:7]=1[NH2:8].[CH:21]1([C:24]2[N:29]=[C:28]([CH:30]=O)[CH:27]=[CH:26][N:25]=2)[CH2:23][CH2:22]1.[S].C(O)(=O)C>C(O)C>[CH:21]1([C:24]2[N:29]=[C:28]([C:30]3[NH:8][C:7]4=[N:6][C:5]([N:9]5[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]([N:17]([CH2:19][CH3:20])[CH3:18])=[O:16])[CH2:10]5)=[CH:4][CH:3]=[C:2]4[N:1]=3)[CH:27]=[CH:26][N:25]=2)[CH2:23][CH2:22]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 5362487SulfurHCID 299398122-Cyclopropylpyrimidine-4-carbaldehydeHCID 117966322(R)-1-(5,6-Diaminopyridin-2-yl)-N-ethyl-N-methylpiperidine-3-carboxamide

Produkt 1

HCID 178464471HCID 178464471, VerbindungAusbeute 13,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of (R)-1-(5,6-diaminopyridin-2-yl)-N-ethyl-N-methylpiperidine-3-carboxamide (200 mg, 0.722 mmol) in ethanol (10 mL) was added 2-cyclopropylpyrimidine-4-carbaldehyde (106 mg, 0.722 mmol), sulfur powder (69 mg, 2.16 mmol), and acetic acid (0.2 mL). The reaction mixture was heated to 80° C. for 18 h. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. The organic layer was concentrated under reduced pressure. The crude material was purified via preparative HPLC to afford the title compound (40 mg, 13.5%). 1H NMR (300 MHz, CDCl3) δ 1.09-1.18 (m, 3H), 1.19-1.31 (m, 4H), 1.65-1.73 (m, 1H), 1.84 (d, 1H), 1.88-1.98 (m, 2H), 2.31 (d, 1H), 2.69-2.87 (m, 1H), 2.99 (br s, 1H), 3.03 (br s, 1H), 3.11 (br s, 1H), 3.14-3.27 (m, 1H), 3.37-3.57 (m, 2H), 4.37 (d, 1H), 4.45-4.59 (m, 1H), 6.76 (d, 1H), 7.79-7.96 (m, 1H), 8.67 (d, 1H), 10.25 (br s, 1H). MS (ES+APCI) (M+H) 406.3; LCMS retention time 3.055 min (Method U1).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and water
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customThe crude material was purified via preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-13a37c04f9b54c07990faffacbe54a47
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296745B2

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