Triethylamine → HCID 57970179, Verbindung

HRID 1666651Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666651
Cl[C:2]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:25]([N:32]1[CH2:36][CH2:35][C@H:34]([NH2:37])[CH2:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>C(O)(C)C>[CH2:25]([N:32]1[CH2:36][CH2:35][C@H:34]([NH:37][C:2]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:14][CH2:13]3)[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH2:33]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 1519353(3S)-(+)-1-Benzyl-3-aminopyrrolidineHCID 24752963950666-26-9

Produkt 1

HCID 57970179HCID 57970179, VerbindungAusbeute 62,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of t-butyl 4-(2-chloroquinazolin-4-yl)piperazine-1-carboxylate (30 g) synthesized in the same manner as in Example 1, (S)-1-benzyl-3-aminopyrrolidine (15 g), triethylamine (8.7 g), and isopropyl alcohol (43 mL) was heated to reflux for 40 h. The reaction mixture was concentrated under reduced pressure, then water was added to the residue, and the mixture was extracted with chloroform. The organic layer was dried with anhydrous magnesium sulfate, concentrated, and then purified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate=4:1) to obtain t-butyl 4-(2-((S)-1-benzylpyrrolidin-3-ylamino)quinazolin-4-yl)piperazine-1-carboxylate (26 g).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 40 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionwater was added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-746b17b2df514c50bcf2c9f1b55e422c
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044068B2

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