3-Methyl-4-(pyridin-3-yloxy)aniline → 2-Chloro-N-(3-{4-[3-methyl-4-(pyridin-3-yloxy)-phenylamino]-quinazolin-6-yl}-prop-2-ynyl)-acetamide

HRID 2055153Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2055153
[Cl:1][CH2:2][C:3]([NH:5][CH2:6][C:7]#[C:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][N:13]=[C:12]2Cl)=[O:4].[CH3:20][C:21]1[CH:22]=[C:23]([NH2:34])[CH:24]=[CH:25][C:26]=1[O:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1>CC(O)(C)C.ClCCCl>[Cl:1][CH2:2][C:3]([NH:5][CH2:6][C:7]#[C:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][N:13]=[C:12]2[NH:34][C:23]1[CH:24]=[CH:25][C:26]([O:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[C:21]([CH3:20])[CH:22]=1)=[O:4]

Komponenten

4

Edukt 2

HCID 219252673-Methyl-4-(pyridin-3-yloxy)anilineHCID 224843152-Chloro-N-(3-(4-chloroquinazolin-6-yl)prop-2-yn-1-yl)acetamide

Produkt 1

HCID 224841242-Chloro-N-(3-{4-[3-methyl-4-(pyridin-3-yloxy)-phenylamino]-quinazolin-6-yl}-prop-2-ynyl)-acetamideAusbeute 88,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21868497Tert-butyl alcohol 1,2-dichloroethaneLösungsmittel

Versuchsvorschrift

A mixture of 2-Chloro-N-[3-(4-chloro-quinazolin-6-yl)-prop-2-ynyl]-acetamide (0.90 g, 3.05 mmol) and 3-Methyl-4-(pyridin-3-yloxy)-phenylamine (0.61 g, 3.05 mmol) in tBuOH/DCE (5.0/5.0 mL) was refluxed under nitrogen for 40 minutes and concentrated. The residue was dissolved in MeOH (2.0 mL) and added to EtOAc with vigorous stirring to precipitate the HCl salt product as tan solid which was collected by vacuum-filtration, rinsed with EtOAc, and further dried to give 1.24 g (82%) of 2-Chloro-N-(3-{4-[3-methyl-4-(pyridin-3-yloxy)-phenylamino]-quinazolin-6-yl}-prop-2-ynyl)-acetamide: 1H NMR (CD3OD) δ 2.27 (s, 3H), 4.09 (s, 2H), 4.29 (s, 2H), 7.07 (d, 1H), 7.51 (m, 2H), 7.60 (d, 1H), 7.70 (s, 1H), 7.78 (d, 1H), 8.05 (d, 1H), 8.32 (m, 2H), 8.67 (s, 1H), 8.75 (s, 1H); MS m/z (MH+) 458.0.

Aufarbeitung

  1. temperaturewas refluxed under nitrogen for 40 minutes
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in MeOH (2.0 mL)
  4. additionadded to EtOAc
  5. customto precipitate the HCl salt product as tan solid which
  6. filtrationwas collected by vacuum-filtration
  7. washrinsed with EtOAc
  8. customfurther dried

Quellen und Nachweise

ORD-Eintrag
ord-9b56cfb7084249f8930cb5efbffe70c0
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07332493B2

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