N-Methyl-4-anisidine → N-{4-[(4-methoxyphenyl)(methyl)amino]-9H-pyrimido[4,5-b]indol-2-yl}-2,2-dimethylpropanamide

HRID 2172901

Reaktionsgleichung

Reaktionsgleichung von HRID 2172901
Cl[C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[N:5]=[C:4]([NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[N:3]=1.[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([NH:28][CH3:29])=[CH:26][CH:25]=1>>[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([N:28]([CH3:29])[C:2]2[C:14]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[NH:7][C:6]=3[N:5]=[C:4]([NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[N:3]=2)=[CH:26][CH:25]=1

Komponenten

3

Edukt 2

HCID 22250N-Methyl-4-anisidineHCID 57625951N-(4-chloro-9H-pyrimido[4,5-b]indol-2-yl)-2,2-dimethylpropanamide

Produkt 1

HCID 67007332N-{4-[(4-methoxyphenyl)(methyl)amino]-9H-pyrimido[4,5-b]indol-2-yl}-2,2-dimethylpropanamideAusbeute 37 %

Versuchsvorschrift

Using the general procedure described above, the reaction of 6 (180 mg, 0.59 mmol) and 4-methoxy-N-methylaniline (612 mg, 4.46 mmol) was run for 120 hours, to provide 88 mg of 11 as a brown solid in 37% yield. TLC Rf 0.57 (chloroform-methanol 15:1); mp 288.5-289.4° C.; 1H NMR (DMSO-d6) 81.26 (s, 9H, C(CH3)3,) 3.60 (s, 3H, OCH3), 3.69 (s, 3H, NCH3), 5.87-7.33 (m, 8H, Ar—H), 9.58 (s, 1H, 2-NH, exch), 11.88 (s, 1H, 9-NH, exch).

Quellen und Nachweise

ORD-Eintrag
ord-dc1e70ea68294f5aa40290d3533557f9
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056869B2

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