Dichloromethane → 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 2-pyrrolidin-1-yl-ethyl ester

HRID 1008121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1008121
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1/[CH:8]=[C:9]1\[C:10](=[O:25])[N:11]([C:18](N2C=CN=C2)=[O:19])[C:12]2[C:17]\1=[CH:16][CH:15]=[CH:14][CH:13]=2.[N:26]1([CH2:31][CH2:32][OH:33])[CH2:30][CH2:29][CH2:28][CH2:27]1.C(O)(C(F)(F)F)=O.ClCCl>C1COCC1>[N:26]1([CH2:31][CH2:32][O:33][C:18]([N:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)/[C:9](=[CH:8]/[C:3]3[NH:4][C:5]([CH3:7])=[CH:6][C:2]=3[CH3:1])/[C:10]2=[O:25])=[O:19])[CH2:30][CH2:29][CH2:28][CH2:27]1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 762881-PyrrolidineethanolHCID 601112313-[1-(3,5-Dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-1-(imidazol-1-ylcarbonyl)-1,3-dihydro-indol-2-one

Produkt 1

HCID 601112243-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 2-pyrrolidin-1-yl-ethyl esterAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A reaction mixture containing 3-[1-(3,5-dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-1-(imidazol-1-ylcarbonyl)-1,3-dihydro-indole-2-one (166 mg, 0.5 mmol), 2-pyrrolidin-1-yl-ethanol (115 mg, 1.0 mmol), and TFA (0.13 mL, 1.5 mmol) in 2 mL of THF, and 2 mL of dichloromethane gave 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 2-pyrrolidin-1-yl-ethyl ester (28 mg, 15%) as a yellow solid. 1HNMR (400 MHz, DMSO-d6) δ 12.56 (s, br, 1H, N-1′), 7.80-7.86 (m, 2H), 7.64 (s, 1H, H-vinyl), 7.16-7.20 (m, 2H), 6.10 (s, 1H, H-4′), 4.46 (t, J=5.47 Hz, 2H, CH2), 2.83 (m, br, 2H, CH2), 2.56 (m, br, 4H, CH2×2), 2.36 (s, 3H, CH3), 2.33 (s, 3H, CH3), and 1.69 (m, br, 4H, CH2×2)

Quellen und Nachweise

ORD-Eintrag
ord-4a9fdb8748aa45fca0bc6da56e237d39
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06797725B2

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