Triphenylphosphine → 2-(3-chlorophenyl)-3-methyl-6-(quinuclidin-3-yloxy)quinazolin-4(3H)-one

HRID 77410

Reaktionsgleichung

Reaktionsgleichung von HRID 77410
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:17]([CH3:18])[C:16](=[O:19])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:20])[CH:14]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[N:21]12[CH2:28][CH2:27][CH:24]([CH2:25][CH2:26]1)[CH:23](O)[CH2:22]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:17]([CH3:18])[C:16](=[O:19])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:20][CH:23]4[CH:24]5[CH2:27][CH2:28][N:21]([CH2:26][CH2:25]5)[CH2:22]4)[CH:14]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 15381(+-)-3-QuinuclidinolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 699287212-(3-chlorophenyl)-6-hydroxy-3-methylquinazolin-4(3H)-one2×

Produkt 1

HCID 513533152-(3-chlorophenyl)-3-methyl-6-(quinuclidin-3-yloxy)quinazolin-4(3H)-oneAusbeute 12,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-(3-chlorophenyl)-6-hydroxy-3-methylquinazolin-4(3H)-one (Intermediate 33A) (100 mg, 0.35 mmol), 3-quinuclidinol (44 mg, 0.35 mmol) and triphenylphosphine (137 mg, 0.35 mmol) in tetrahydrofuran (2 mL) was added dropwise diisopropyl azodicarboxylate (0.103 mL, 0.52 mmol). The reaction was stirred for 20 h. The mixture was purified by scx cartridge (1 g) followed by acidic prep hplc then scx (500 mg) to afford 2-(3-chlorophenyl)-3-methyl-6-(quinuclidin-3-yloxy)quinazolin-4(3H)-one (18 mg, 0.045 mmol).

Aufarbeitung

  1. customThe mixture was purified by scx cartridge (1 g)

Quellen und Nachweise

ORD-Eintrag
ord-8bfe56b1768448508a09fe381435f52e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841289B2

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