Tetrahydrofuran → N-{4-[3-Chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-3-cyano-quinolin-6-yl}-acrylamide

HRID 1595821

Reaktionsgleichung

[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:22]2[N:23]([CH3:27])[CH:24]=[CH:25][N:26]=2)=[C:17]([Cl:28])[CH:16]=1.[CH2:29]1C[O:32][CH2:31][CH2:30]1.C(N(CC)CC)C.C(Cl)(=O)C=C>CN(C=O)C>[Cl:28][C:17]1[CH:16]=[C:15]([NH:14][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:31](=[O:32])[CH:30]=[CH2:29])[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:12]#[N:13])[CH:20]=[CH:19][C:18]=1[S:21][C:22]1[N:23]([CH3:27])[CH:24]=[CH:25][N:26]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Dissolved most of 1.00 g (2.46 mmol) 6-amino-4-[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-quinoline-3-carbonitrile in 3.5 ml hot DMF, added 12 ml THF and chilled to 0° C. Added 377 μl triethyl amine and 225 μl (2.70 mmol) acryloyl chloride. Removed ice bath at 15 minutes and stripped solvent at 2 hours. Slurried residue in water, collected solids and air dried overnight. Boiled in ethyl acetate, collected solids and dried in vacuo, giving 670 mg of yellow-brown solid: mass spectrum (electrospray m/e): M+H=461.1, 462.2.

Aufarbeitung

customat 2 hours
customSlurried residue in water, collected solids and air
customdried overnight
customBoiled in ethyl acetate, collected solids
customdried in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-12720dc9c1a542aeb74e6346eb69ab76
Quelldatensatz: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06288082B1

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