Diisopropanolamine → 4-[Bis-(2-hydroxy-propyl)-amino]-but-2-enoic Acid [4-(3-chloro-4-fluoro-phenylamino)-3-cyano-7-methoxy-quinolin-6-yl]-amide

HRID 379188

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:27][CH3:28])=[C:17]([NH:20][C:21](=[O:26])[CH:22]=[CH:23][CH2:24]Br)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:29]#[N:30])[CH:5]=[CH:6][C:7]=1[F:8].[NH:31]([CH2:36][CH:37]([OH:39])[CH3:38])[CH2:32][CH:33]([OH:35])[CH3:34].C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:27][CH3:28])=[C:17]([NH:20][C:21](=[O:26])[CH:22]=[CH:23][CH2:24][N:31]([CH2:36][CH:37]([OH:39])[CH3:38])[CH2:32][CH:33]([OH:35])[CH3:34])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:29]#[N:30])[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A mixture of 250 mg (0.51 mmol) of 4-bromo-but-2-enoic acid[4-(3-chloro-4-fluoro-phenylamino)-3-cyano-7-methoxy-quinolin-6-yl]-amide, and 136 mg (1.02 mmol) of 1,1′-iminodi-2-propanol in 2.25 ml dimethylformamide was stirred at room temperature for 3 hr and at 60° C. for 2 hr. After the mixture was cooled, saturated sodium bicarbonate solution was added and the solution was subsequently extracted with ethyl acetate. The extracts were evaporated to an oil, washed with hexane and dried under reduced pressure. Yield 240.1 mg (87%) tan solid: mp 122-125° C.

Aufarbeitung

temperatureAfter the mixture was cooled
extractionthe solution was subsequently extracted with ethyl acetate
customThe extracts were evaporated to an oil
washwashed with hexane
customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-c07c2ed1c7a244ba96f1ae2a2532ba75
Quelldatensatz: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06297258B1

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