Acetic Acid → HCID 178419984, Verbindung

HRID 931228Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 931228
Cl.Cl.[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([N:11]2[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=O)[CH2:12]2)=[N:8][C:9]=1[NH2:10].C(O)(=O)C.[CH2:28]([N:30](CC)CC)C.[CH:35]1([C:38]2[N:43]=[C:42]([C:44](=N)OCC)[CH:41]=[CH:40][N:39]=2)[CH2:37][CH2:36]1>C(O)C>[CH:35]1([C:38]2[N:43]=[C:42]([C:44]3[NH:10][C:9]4=[N:8][C:7]([N:11]5[CH2:16][CH2:15][CH2:14][CH:13]([C:17]6[N:19]7[CH2:23][CH2:22][CH2:21][C:20]7=[CH:28][N:30]=6)[CH2:12]5)=[CH:6][CH:5]=[C:4]4[N:3]=3)[CH:41]=[CH:40][N:39]=2)[CH2:36][CH2:37]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 89853790(1-(5,6-Diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochlorideHCID 89854162Ethyl 2-cyclopropylpyrimidine-4-carbimidate

Produkt 1

HCID 178419984HCID 178419984, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of (1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride (18 mg, 0.06 mmol) and acetic acid (55 μL, 0.96 mmol) in ethanol (0.5 mL) was added triethylamine (17 μL, 0.12 mmol) followed by ethyl 2-cyclopropylpyrimidine-4-carbimidate (11.5 mg, 0.06 mmol) dissolved in ethanol (0.5 mL). The reaction mixture was heated to 70° C. for 1.25 h. The solvent was removed under reduced pressure. The residue was suspended in ethyl acetate and the undissolved solids were filtered off. The filtrate was washed with a saturated aqueous solution of ammonium chloride, washed with a saturated aqueous solution of sodium bicarbonate, and washed with brine. The organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via HPLC to afford the title compound. MS (ESI+) (M+H) 427.1; HPLC retention time 2.0183 (Method A).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. filtrationthe undissolved solids were filtered off
  3. washThe filtrate was washed with a saturated aqueous solution of ammonium chloride
  4. washwashed with a saturated aqueous solution of sodium bicarbonate
  5. washwashed with brine
  6. dry with materialThe organics were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was purified via HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a22db86a9f0c41c993bf0a509ed7154a
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296745B2

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