Triethylamine → HCID 86636517, Verbindung

HRID 1513451Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1513451
Cl.[C:2]([O:6][C:7]([N:9]1[CH2:12][CH:11]([CH2:13][NH2:14])[CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].CCN(CC)CC.[Cl:22][C:23]1[N:28]=[C:27](Cl)[N:26]=[C:25]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[N:24]=1>C1COCC1>[C:2]([O:6][C:7]([N:9]1[CH2:12][CH:11]([CH2:13][NH:14][C:27]2[N:28]=[C:23]([Cl:22])[N:24]=[C:25]([N:30]3[CH2:31][CH2:32][O:33][CH2:34][CH2:35]3)[N:26]=2)[CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 810762,4-Dichloro-6-morpholino-1,3,5-triazineHCID 45072199tert-Butyl 3-(aminomethyl)azetidine-1-carboxylate--hydrogen chloride (1/1)

Produkt 1

HCID 86636517HCID 86636517, VerbindungAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of the 3-aminomethyl-azetidine-1-carboxylic acid tert-butyl ester HCl salt (945 mg, 4.24 mmol) and NEt3 (856 mg, 8.48 mmol) in THF (10 mL) at 0° C. was added a suspension of 2,4-dichloro-6-morpholin-4-yl-[1,3,5]triazine (996 mg, 4.24 mmol) at 0° C. The reaction mixture was stirred for another 1 hr at 0° C. and allowed to warm to 20° C. and stirred for 1-4 hrs to drive the reaction to completion. Silica gel (20 g) was added to the reaction mixture and the solvent was removed so that product was adsorbed on the silica gel. The silica gel plug was placed on top of a column to purify by flash chromatography using CH2Cl2/MeOH/NH3 (20:1:01) eluent. After unifying the product fraction, and evaporation of solvent, (750 mg, 46% yield) product was obtained as yellow solid; MS (ESI) m/z 385

Aufarbeitung

  1. temperatureto warm to 20° C.
  2. stirringstirred for 1-4 hrs
  3. customthe reaction to completion
  4. additionSilica gel (20 g) was added to the reaction mixture
  5. customthe solvent was removed so that product
  6. customto purify by flash chromatography
  7. customthe product fraction, and evaporation of solvent

Quellen und Nachweise

ORD-Eintrag
ord-02662a9d5bd049ef976fbaf35f1841a4
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217036B2

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