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N-methyl-2-pyrrolidone → 4-[4-({3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-6-yl]benzoic acid hydrochloride

HRID 1786940
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1786940
Cl.[Cl:2][C:3]1[C:4]2[NH:11][C:10]([C:12]3[CH:22]=[CH:21][C:15]([C:16]([O:18]CC)=[O:17])=[CH:14][CH:13]=3)=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1.[CH3:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[O:31][C:32]1[CH:33]=[N:34][C:35]([CH3:38])=[CH:36][CH:37]=1)[NH2:27].C(N(C(C)C)CC)(C)C.CN1CCCC1=O>C(OCC)(=O)C.O>[ClH:2].[CH3:23][C:24]1[CH:25]=[C:26]([NH:27][C:3]2[C:4]3[NH:11][C:10]([C:12]4[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:21][CH:22]=4)=[CH:9][C:5]=3[N:6]=[CH:7][N:8]=2)[CH:28]=[CH:29][C:30]=1[O:31][C:32]1[CH:33]=[N:34][C:35]([CH3:38])=[CH:36][CH:37]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 114244343-Methyl-4-((6-methylpyridin-3-yl)oxy)anilineHCID 86615760ethyl 4-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-6-yl)benzoate hydrochloride

Produkt 1

HCID 675204054-[4-({3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-6-yl]benzoic acid hydrochloride
Ausbeute 57,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of ethyl 4-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-6-yl)benzoate hydrochloride (1.297 g), 3-methyl-4-[(6-methylpyridin-3-yl)oxy]aniline (1.00 g), diisopropylethylamine (0.834 g) and 1-methyl-2-pyrrolidinone (12.5 mL) was stirred at 140° C. for 3 hrs, poured into water (100 mL)-ethyl acetate (150 mL) and the precipitated solid was collected by filtration. The solid washed with ethyl acetate and dried under reduced pressure at 60° C. The obtained solid was suspended in methanol (40 mL), and 1N aqueous sodium hydroxide solution (20 mL) was added. After stirring at room temperature for 12 hrs, the solvent was evaporated under reduced pressure, and the residue was adjusted to pH 2 with 1N hydrochloric acid. The precipitated solid was collected by filtration, washed with water and dried under reduced pressure at 60° C. to give the title compound (1.08 g).

Aufarbeitung

  1. filtrationthe precipitated solid was collected by filtration
  2. washThe solid washed with ethyl acetate
  3. customdried under reduced pressure at 60° C
  4. addition1N aqueous sodium hydroxide solution (20 mL) was added
  5. stirringAfter stirring at room temperature for 12 hrs
  6. customthe solvent was evaporated under reduced pressure
  7. filtrationThe precipitated solid was collected by filtration
  8. washwashed with water
  9. customdried under reduced pressure at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-e690e0d37b5647b480ee3cba21bcd7dd
Quelldatensatz
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07507740B2

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