4-((3-Chloro-4-fluorophenyl)amino)-7-methyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one → 3-{5-[4-(3-Chloro-4-fluoro-phenylamino)-7-methyl-6-oxo-6,7-dihydro-pyrrolo [2,3-D]pyrimidin-5-ylidenemethyl]-4-methyl-1H-pyrrol-2-YL}-propionic acid

HRID 397422Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 397422
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[CH2:18][C:17](=[O:19])[N:16]([CH3:20])[C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH:21]([C:23]1[CH:24]([CH3:33])[CH:25]=[C:26]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[N:27]=1)=O>N1CCCCC1.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18](=[CH:21][C:23]4[NH:27][C:26]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:25][C:24]=4[CH3:33])[C:17](=[O:19])[N:16]([CH3:20])[C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

5

Edukt 2

HCID 223909724-((3-Chloro-4-fluorophenyl)amino)-7-methyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-oneHCID 230001443-(5-formyl-4-methyl-4H-pyrrol-2-yl)-propionic acid

Produkt 1

HCID 698155343-{5-[4-(3-Chloro-4-fluoro-phenylamino)-7-methyl-6-oxo-6,7-dihydro-pyrrolo [2,3-D]pyrimidin-5-ylidenemethyl]-4-methyl-1H-pyrrol-2-YL}-propionic acidAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8082PiperidineKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-(3-Chloro-4-fluoro-phenylamino)-7-methyl-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (100 mg, 0.34 mmol) was condensed with 3-(5-formyl-4-methyl-4H-pyrrol-2-yl)-propionic acid (62 mg, 0.41 mmol) and piperidine (2 drops) in ethanol (3 mL) stirred at 80° C. for 2 hours to give 31 mg (20%) of the title compound. 1H NMR (360 MHz, DMSO-d6) δ 13.14 (br s, 1H, NH), 9.14 (s, 1H), 8.34 (s, 1H), 7.69 (m, 1H), 7.30-7.40 (m, 3H), 6.08 (s, 1H), 3.32 (s, 3H, CH3), 2.89 (m, 2H, CH2), 2.53 (m, 2H, CH2), 2.16 (s, 3H, CH3).

Quellen und Nachweise

ORD-Eintrag
ord-a073766cc2a94f039be03c23eb30adf0
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610688B2

Notizen zur Reaktion

Wird geladen…