Triethylamine → N-[4-Chloro-3-(4-methylpiperazin-1-yl)phenyl]-N'-[4-(pyridin-4-yl)naphth-1-yl]urea

HRID 1275017

Reaktionsgleichung

Reaktionsgleichung von HRID 1275017
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[N:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([NH2:29])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.C(N(CC)CC)C.[Cl:37][C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[CH:40][C:39]=1[N:45]1[CH2:50][CH2:49][N:48]([CH3:51])[CH2:47][CH2:46]1>ClCCl>[Cl:37][C:38]1[CH:44]=[CH:43][C:41]([NH:42][C:2]([NH:29][C:22]2[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:19]([C:16]3[CH:15]=[CH:14][N:13]=[CH:18][CH:17]=3)=[CH:20][CH:21]=2)=[O:4])=[CH:40][C:39]=1[N:45]1[CH2:46][CH2:47][N:48]([CH3:51])[CH2:49][CH2:50]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 108570124-(Pyridin-4-yl)naphth-1-ylamineHCID 181800734-Chloro-3-(4-methylpiperazin-1-yl)aniline

Produkt 1

HCID 22118919N-[4-Chloro-3-(4-methylpiperazin-1-yl)phenyl]-N'-[4-(pyridin-4-yl)naphth-1-yl]urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of triphosgene (39 mg, 0.13 mmole) in dichloromethane (10 ml) was added a solution of 4-(pyridin-4-yl)naphth-1-ylamine (D1, 82 mg, 0.37 mmole) and triethylamine (0.05 ml, 0.37 mmole) dropwise over 30 minutes. When the addition was complete the mixture was stirred at room temperature for 15 minutes, then a solution of 4-chloro-3-(4-methylpiperazin-1-yl)aniline (100 mg, 0.44 mmole, EP0533268A1) in dichloromethane (10 ml) was added over 5 minutes. After 18 h, the mixture was washed with 10% aqueous sodium carbonate solution and water, dried (Na2SO4) and evaporated to dryness. The residue was purified by column chromatography on silica gel eluting with 10% methanol/dichloromethane and the title compound was obtained as a white solid on trituration with ether (47 mg, 27%).

Aufarbeitung

  1. additionWhen the addition
  2. waitAfter 18 h
  3. washthe mixture was washed with 10% aqueous sodium carbonate solution and water
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography on silica gel eluting with 10% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-58d818f6374b4e928a506fea67f2417a
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06159979

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