Ammonia → 3-Cyclopentyl-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-8-ylamine

HRID 449028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449028
[NH3:1].Cl[C:3]1[C:4]2[N:5]([C:9]([CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[N:10][C:11]=2[C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[CH:6]=[CH:7][N:8]=1>O.CC(O)C>[CH:25]1([C:9]2[N:5]3[CH:6]=[CH:7][N:8]=[C:3]([NH2:1])[C:4]3=[C:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:13]=3)[N:10]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1

Komponenten

5

Edukt 2

HCID 222AmmoniaHCID 866360308-Chloro-3-cyclopentyl-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazine

Produkt 1

HCID 210368713-Cyclopentyl-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-8-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

20 M NH3 in H2O (2 mL) was added to a suspension of 8-chloro-3-cyclopentyl-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazine (21 mg, 0.054 mmol) in i-PrOH (2 mL). The mixture was heated in an oil bath set at 105° C. overnight. Reaction mixture was concentrated in vacuo and purification by prep TLC using 10% MeOH in DCM afforded 9 mg of the title compound as an off white solid. The compound was registered as OSIP 700099. 1H NMR (400 MHz, CDCl3): δ=1.61-1.95 (m, 4H), 2.02-2.23 (m, 4H), 3.30-3.43 (m, 1H), 5.07 (br. s., 2H), 7.03-7.08 (m, 3H), 7.08-7.16 (m, 3H), 7.23 (d, J=5.05 Hz, 1H), 7.30-7.41 (m, 2H), 7.61 (d, 2H). MS (ES+): m/z 370.83 (100)[MH+]. HPLC: tR=2.61 min (Open Lynx polar—5 min).

Aufarbeitung

  1. temperatureThe mixture was heated in an oil bath
  2. customReaction mixture
  3. concentrationwas concentrated in vacuo and purification by prep TLC

Quellen und Nachweise

ORD-Eintrag
ord-0592626016c0482498a7be3ee7ecca69
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481733B2

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