Phenyl (1-phenyl-1H-pyrazol-5-yl)carbamate → (8aS)-1,3-dioxo-2-[(1S,2R)-2-phenylcyclopropyl]-N-(1-phenyl-1H-pyrazol-5-yl)hexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxamide

HRID 1260472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1260472
Cl.[C:2]1([C@H:8]2[CH2:10][C@@H:9]2[N:11]2[C:19](=[O:20])[C@@H:14]3[CH2:15][NH:16][CH2:17][CH2:18][N:13]3[C:12]2=[O:21])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1([N:28]2[C:32]([NH:33][C:34](=O)[O:35]C3C=CC=CC=3)=[CH:31][CH:30]=[N:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[O:20]=[C:19]1[C@@H:14]2[CH2:15][N:16]([C:34]([NH:33][C:32]3[N:28]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:29]=[CH:30][CH:31]=3)=[O:35])[CH2:17][CH2:18][N:13]2[C:12](=[O:21])[N:11]1[C@H:9]1[CH2:10][C@@H:8]1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 57925698Phenyl (1-phenyl-1H-pyrazol-5-yl)carbamateHCID 67300061(8aS)-2-[(1S,2R)-2-Phenylcyclopropyl]tetrahydroimidazo[1,5-a]pyrazine-1,3(2H,5H)-dione HCl salt

Produkt 1

HCID 56662793(8aS)-1,3-dioxo-2-[(1S,2R)-2-phenylcyclopropyl]-N-(1-phenyl-1H-pyrazol-5-yl)hexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxamideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Example 4, D2 (1 eq) was dissolved in DCM (0.1M), F3 (1.5 eq) and TEA (1.5 eq) were added and the reaction was stirred at RT 6 h. The reaction was diluted with DCM and washed with water and brine, dried and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with 10-100% EtOAc/petroleum ether to afford the title compound in 85% yield. 1H NMR (400 MHz, DMSO-d6, 300K) δ 8.91 (1H, s), 7.62 (1H, d, J=1.7 Hz), 7.54-7.47 (4H, m), 7.37 (1H, m), 7.30 (2H, m), 7.22-7.20 (3H, m), 6.31 (1H, d, J=1.7 Hz), 4.24 (1H, m), 4.02-3.96 (2H, m), 3.87 (1H, m), 2.97 (1H, m), 2.84 (2H, m), 2.67 (1H, m), 2.38 (1H, m), 1.52-1.48 (1H, m), 1.40 (1H, m). MS (ES+) C25H24N6O3 requires 456, found: 457 (M+H+).

Aufarbeitung

  1. washwashed with water and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by flash chromatography on silica gel eluting with 10-100% EtOAc/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-711bf8d7397242fe89202c926ac99457
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470823B2

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