Dichloromethane → [4-(5-(Cyclopropyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene-2-yl-ethynyl)-2-fluoro-phenyl] acetic acid ethyl ester

HRID 278649

Reaktionsgleichung

Reaktionsgleichung von HRID 278649
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:23]=[CH:22][C:21]3[C:20](=O)[CH2:19][CH2:18][C:17]([CH3:26])([CH3:25])[C:16]=3[CH:15]=2)=[CH:8][C:7]=1[F:27])[CH3:2].ClCCl.[CH:32]1([NH2:35])[CH2:34][CH2:33]1.C([BH3-])#N.[Na+]>CCCCCC.C(OCC)(=O)C.C(O)(=O)C.C(#N)C>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:23]=[CH:22][C:21]3[CH:20]([NH:35][CH:32]4[CH2:34][CH2:33]4)[CH2:19][CH2:18][C:17]([CH3:26])([CH3:25])[C:16]=3[CH:15]=2)=[CH:8][C:7]=1[F:27])[CH3:2]

Komponenten

9

Edukt 4

HCID 6344DichloromethaneHCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 69548870[2-Fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalene-2-ylethynyl)phenyl]acetic acid ethyl ester2×

Produkt 1

HCID 69548141[4-(5-(Cyclopropyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene-2-yl-ethynyl)-2-fluoro-phenyl] acetic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Following general procedure G and using [2-fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalene-2-ylethynyl) phenyl]acetic acid ethyl ester (Compound 14, 0.258 g, 0.68 mmol), dichloromethane (4 mL), acetonitrile(2 mL), cyclopropyl amine(1 mL, 14.45 mmol), acetic acid (1 mL)and sodium cyanoborohydride (0.266 g, 4.23 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 16-20-25% ethyl acetate in hexane as the eluent, the title compound was obtained as a pale yellow oil (0.21 g, 73%).

Quellen und Nachweise

ORD-Eintrag
ord-4520212d4505447d9193d13a60c3b107
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06359135B1

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