3,4-Difluorobenzylamine → tert-butyl (3aR,7aS)-2-[(3,4-difluorophenyl)methylamino]-3a,4,5,6,7,7a-hexahydrobenzimidazole-1-carboxylate

HRID 18749

Reaktionsgleichung

CS[C:3]1[N:7]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:6]2[CH2:15][CH2:16][CH2:17][CH2:18][C@H:5]2[N:4]=1.[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:23][NH2:24]>ClCCl>[C:11]([O:10][C:8]([N:7]1[C@H:6]2[CH2:15][CH2:16][CH2:17][CH2:18][C@H:5]2[N:4]=[C:3]1[NH:24][CH2:23][C:22]1[CH:25]=[CH:26][C:27]([F:28])=[C:20]([F:19])[CH:21]=1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of intermediate 76 (200 mg, 0.740 mmol), 3,4-difluorobenzylamine (0.5 mL, 4.2 mmol) is heated at 100° C. (reaction block) overnight. The reaction mixture is cooled to RT. The reaction mixture is diluted with dichloromethane, washed with 0.1N HCl, and brine. The solvent is evaporated, and the residue triturated with EtOAc, and the insoluble material filtered to give 270 mg of the product 195. 1H NMR (CDCl3) δ 8.60 (s, 1 H), 7.40-7.10 (m, 3 H), 5.15-4.90 (m, 2 H), 4.30-4.10 (m, 2 H), 2.70-2.55 (m, 1 H), 2.20-2.05 (m, 1 H), 1.85-1.10 (m, 15 H); MS: m/z 366 (M++1).

Aufarbeitung

custom(reaction block) overnight
temperatureThe reaction mixture is cooled to RT
washwashed with 0.1N HCl, and brine
customThe solvent is evaporated
customthe residue triturated with EtOAc
filtrationthe insoluble material filtered

Quellen und Nachweise

ORD-Eintrag: ord-e28b7ea43af34b80a87b9ebc21e193e0
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07741493B2

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