Cyclopropylamine → 2-Amino-cyclopropylamino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2080202Notizen

Reaktionsgleichung

[NH2:1][C:2]1[N:23]=[C:22](Cl)[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5].C1C=CC(CC(NCN[C@H](C(O)=O)CC2[CH:44]=[CH:43][C:42]([N+:45]([O-])=O)=CC=2)=O)=CC=1.C1(N)CC1>CS(C)=O.C(N(CC)C(C)C)(C)C.[Cl-].[Na+].O>[NH2:1][C:2]1[N:23]=[C:22]([NH:45][CH:42]2[CH2:44][CH2:43]2)[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5]

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

2-Amino-6-chloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide described in Example A-101 (30 mg, 0.083 mmol) was dissolved in a mixture solution of dimethylsulfoxide (1 mL) and N,N-diisopropylethylamine (0.5 mL), cyclopropylamine (0.058 mL, 0.84 mmol) was added thereto, followed by heating in a sealed tube for 15 hours 30 minutes (oil bath temperature: 130° C.). The reaction mixture was allowed to room temperature, poured into brine, which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then concentrated, the obtained residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=2:1), and the title compound (15 mg, 0.039 mmol, 47.5%) was obtained.

Aufarbeitung

additionwas added
customwas allowed to room temperature
extractionwas then extracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated
customthe obtained residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=2:1)

Quellen und Nachweise

ORD-Eintrag: ord-10b4597d1c894627866eb85a8509fa9d
Quelldatensatz: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07932272B2

Notizen zur Reaktion

Wird geladen…