Sodium Hydroxide → HCID 25233117, Verbindung

HRID 2167937

Reaktionsgleichung

Reaktionsgleichung von HRID 2167937
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:30])[C:10]2[C:22]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15][C:14]=3[N:13]=[C:12]([NH:23]C(=O)C(C)(C)C)[N:11]=2)=[CH:5][CH:4]=1.[OH-].[Na+].ClC1C2C3C(=CC=CC=3)NC=2N=C(NC(=O)C(C)(C)C)N=1.COC1C=C(C=CC=1)NC>Cl.C(Cl)(Cl)Cl.CO.C(O)CCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH3:30])[C:10]2[C:22]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15][C:14]=3[N:13]=[C:12]([NH2:23])[N:11]=2)=[CH:7][CH:8]=1

Komponenten

8

Edukt 4

HCID 14798Sodium HydroxideHCID 84349N-Methyl-m-anisidineHCID 57625951N-(4-chloro-9H-pyrimido[4,5-b]indol-2-yl)-2,2-dimethylpropanamideHCID 67007332N-{4-[(4-methoxyphenyl)(methyl)amino]-9H-pyrimido[4,5-b]indol-2-yl}-2,2-dimethylpropanamide

Produkt 1

HCID 25233117HCID 25233117, VerbindungAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 2631-ButanolLösungsmittelHCID 21584188Chloroform methanolLösungsmittel

Versuchsvorschrift

Using the general procedure described above, the reaction of 11 (100 mg, 0.24 mmol) and 1 N NaOH provided 58 mg of AAG107 as a white solid in 73% yield. Alternatively, AAG107 can also be synthesized by treating 6 (90 mg, 0.3 mmol) with 3-methoxy-N-methylaniline (306 mg, 2.23 mmol) in presence of 3 drops HCl and solvent n-butanol under reflux conditions for 14 hours. The yield from 6 to AAG107 using this method is 53%. TLC Rf 0.34 (chloroform-methanol 15:1); mp 233.6° C.; 1H NMR (DMSO-d6) δ 3.55 (s, 3H, OCH3), 3.58 (s, 3H, NCH3), 6.19 (s, 2H, NH2, exch), 5.87-7.18 (m, 8H, Ar—H), 11.27 (s, 1H, 9-NH, exch).

Aufarbeitung

  1. customprovided 58 mg of AAG107 as a white solid in 73% yield
  2. customAlternatively, AAG107 can also be synthesized
  3. customThe yield from 6 to AAG107

Quellen und Nachweise

ORD-Eintrag
ord-59f2b0d54b454dbf91c4f1a044809ad7
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045489B2

Verknüpfte Notizen

Wird geladen…