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Ethanol → (3S,6R)-1-[2-Amino-6-(3-amino-1H-indazol-6-yl)-4-pyrimidinyl]-N-[(1R)-1-cyclohexylethyl]-6-methyl-3-piperidinecarboxamide

HRID 2367490
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2367490
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C@H:13]([CH3:14])[CH2:12][CH2:11][C@H:10]([C:15]([NH:17][C@@H:18]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH3:19])=[O:16])[CH2:9]2)[CH:5]=[C:4]([C:26]2[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[C:28](F)[CH:27]=2)[N:3]=1.CCO.CCN(C(C)C)C(C)C.[NH2:47][NH2:48]>O.CO>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C@H:13]([CH3:14])[CH2:12][CH2:11][C@H:10]([C:15]([NH:17][C@@H:18]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH3:19])=[O:16])[CH2:9]2)[CH:5]=[C:4]([C:26]2[CH:27]=[C:28]3[C:29]([C:32]([NH2:33])=[N:47][NH:48]3)=[CH:30][CH:31]=2)[N:3]=1
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Komponenten

7

Edukt 4

HCID 702EthanolHCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 58504811(3S,6R)-1-[2-Amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-[(1R)-1-cyclohexylethyl]-6-methyl-3-piperidinecarboxamide

Produkt 1

HCID 58504746(3S,6R)-1-[2-Amino-6-(3-amino-1H-indazol-6-yl)-4-pyrimidinyl]-N-[(1R)-1-cyclohexylethyl]-6-methyl-3-piperidinecarboxamide
Ausbeute 50,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Into a microwave tube, (3S,6R)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-[(1R)-1-cyclohexylethyl]-6-methyl-3-piperidinecarboxamide (195.6 mg, 0.421 mmol), 5 mL of EtOH, Hunig's base (0.294 mL, 1.684 mmol), and hydrazine anhydrous (0.079 mL, 2.53 mmol) were added, and the yellow suspension mixture was heated overnight at 110° C. in an oil bath. LCMS showed mainly product. CH3OH (5 mL) was added to the solution. The black solid and the yellow solution were carefully separated due to the black solid is heavier than yellow solution. Water (20 mL) was added to the yellow solution, and a solid formed. The solid was filtered, washed by water and dried in vacuum. The solid was recrystallized using CH3CN, and the solid in the solvent was filtered, washed by EtOAc and CH3CN, and dried in vacuum to afford the title compound (102 mg) as a light yellow solid. LC-MS (ES) m/z=477 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.83-1.36 (m, 12H), 1.55-1.85 (m, 9H), 2.20-2.37 (m, 1H), 2.92 (m, 1H), 3.56-3.71 (m, 1H), 5.38 (s, 2H), 6.07 (s, 2H), 6.57 (s, 1H), 7.54-7.61 (m, 1H), 7.66-7.78 (m, 2H), 7.94 (s, 1H), 11.50 (s, 1H).

Aufarbeitung

  1. customa solid formed
  2. filtrationThe solid was filtered
  3. washwashed by water
  4. customdried in vacuum
  5. customThe solid was recrystallized
  6. filtrationthe solid in the solvent was filtered
  7. washwashed by EtOAc and CH3CN
  8. customdried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6a5d0ff2ef874331a3195f9ee4d6d403
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08697685B2

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