Hydrazine → HCID 178508271, Verbindung

HRID 2367380Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2367380
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10](F)[CH:9]=2)[CH:5]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH:19]([C:23]3[NH:24][C:25]4[CH:30]=[CH:29][N:28]=[CH:27][C:26]=4[N:31]=3)[CH2:18]2)[N:3]=1.[NH2:32][NH2:33]>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:11]([C:12]([NH2:13])=[N:32][NH:33]3)=[CH:14][CH:15]=2)[CH:5]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH:19]([C:23]3[NH:24][C:25]4=[CH:30][CH:29]=[N:28][CH:27]=[C:26]4[N:31]=3)[CH2:18]2)[N:3]=1

Komponenten

4

Edukt 2

HCID 9321HydrazineHCID 178509576HCID 178509576, Verbindung

Produkt 1

HCID 178508271HCID 178508271, VerbindungAusbeute 6,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 4-{2-amino-6-[2-(1H-imidazo[4,5-c]pyridin-2-yl)-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (380 mg, 0.913 mmol) and hydrazine (1.432 mL, 45.6 mmol) in ethanol (3 mL) was heated under microwave conditions with stirring for 1 hour. The mixture was concentrated. Water (20 mL) was added, and the resulting mixture was filtered to afford the crude title compound (135 mg) as a brown solid. This material was combined with another sample of the title compound (25 mg), and the combined material was purified by preparative HPLC using CH3CN in water (10 mmol ammonium hydrogen carbonate in water) from 40% to 60% in 9 min to afford the title compound (21 mg) as an off-white solid. LC-MS (ES) m/z=429 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 3.13-3.22 (m, 2H), 3.81-3.91 (m, 1H), 4.14 (d, J=11.2 Hz, 1H), 4.34 (d, J=11.6 Hz, 1H), 4.91 (dd, J=10.0 Hz, 2H), 5.39 (s, 2H), 6.25 (s, 2H), 6.72 (s, 1H), 7.54 (s, 1H), 7.62 (m, 1H), 7.72 (d, J=8.8 Hz, 1H), 7.97 (s, 1H), 8.31 (d, J=5.6 Hz, 1H), 8.91 (s, 1H), 11.54 (s, 1H), 13.01 (s, 1H).

Aufarbeitung

  1. temperaturewas heated under microwave conditions
  2. concentrationThe mixture was concentrated
  3. additionWater (20 mL) was added
  4. filtrationthe resulting mixture was filtered
  5. customto afford the crude title compound (135 mg) as a brown solid

Quellen und Nachweise

ORD-Eintrag
ord-31829f1c13d440b9be4611039cd70565
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697685B2

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