Water → N1-(2-dimethylaminoethyl)-N4-[4-(1H-indol-3-yl)pyrimidin-2-yl]-5-methoxy-N1-methylbenzene-1,2,4-triamine

HRID 1842820

Reaktionsgleichung

Reaktionsgleichung von HRID 1842820
O.[CH3:2][N:3]([CH3:35])[CH2:4][CH2:5][N:6]([CH3:34])[C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][C:10]([NH:16][C:17]2[N:22]=[C:21]([C:23]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[NH:25][CH:24]=3)[CH:20]=[CH:19][N:18]=2)=[C:9]([O:32][CH3:33])[CH:8]=1.[NH4+].[Cl-]>[Fe].C(O)C>[CH3:35][N:3]([CH3:2])[CH2:4][CH2:5][N:6]([CH3:34])[C:7]1[C:12]([NH2:13])=[CH:11][C:10]([NH:16][C:17]2[N:22]=[C:21]([C:23]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[NH:25][CH:24]=3)[CH:20]=[CH:19][N:18]=2)=[C:9]([O:32][CH3:33])[CH:8]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 71240878N1-(4-(1H-indol-3-yl)pyrimidin-2-yl)-N4-(2-(dimethylamino)ethyl)-2-methoxy-N4-methyl-5-nitrobenzene-1,4-diamine2×

Produkt 1

HCID 86677322N1-(2-dimethylaminoethyl)-N4-[4-(1H-indol-3-yl)pyrimidin-2-yl]-5-methoxy-N1-methylbenzene-1,2,4-triamineAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

Water (4 mL) was added in one portion to a mixture of N′-(2-dimethylaminoethyl)-N-[4-(1H-indol-3-yl)pyrimidin-2-yl]-2-methoxy-N′-methyl-5-nitrobenzene-1,4-diamine (Intermediate 169, 270 mg, 0.59 mmol), iron (196 mg, 3.51 mmol), NH4Cl (21.9 mg, 0.41 mmol) and ethanol (24 mL). The resulting mixture was heated at 105° C. for 3 h then filtered through diatomaceous earth (Celite™). The filtrate was concentrated in vacuo and then part-purified by ion exchange chromatography, using an SCX column and eluting with 0.35M methanolic ammonia. Appropriate fractions were combined and concentrated in vacuo to give the title compound (244 mg, 97%) as a brown solid which was used without further purification; 1H NMR: 2.18 (6H, s), 2.37 (2H, s), 2.64 (3H, s), 2.90 (2H, s), 3.76 (3H, s), 6.77 (1H, s), 7.03-7.26 (3H, m), 7.46 (1H, d), 7.52 (1H, s), 7.74 (1H, s), 8.18-8.35 (2H, m), 8.42 (1H, d), 11.72 (1H, s); m/z: ES+ MH+ 432.

Aufarbeitung

  1. filtrationthen filtered through diatomaceous earth (Celite™)
  2. concentrationThe filtrate was concentrated in vacuo
  3. custompart-purified by ion exchange chromatography
  4. washeluting with 0.35M methanolic ammonia
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f952effef33245baad8aac300087ba72
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946235B2

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