Acetic Acid → 2-(4-Cyclopropylpiperazin-1-yl)-5-pyrrolidin-1-ylmethylbenzooxazole

HRID 1619277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619277
[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[O:11][C:12]4[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO.C1COCC1>[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[O:11][C:12]4[CH:18]=[CH:17][C:16]([CH2:19][N:21]5[CH2:25][CH2:24][CH2:23][CH2:22]5)=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 5003444Sodium cyanoborohydrideHCID 595887962-(4-Cyclopropylpiperazin-1-yl)benzooxazole-5-carboxaldehyde

Produkt 1

HCID 237289312-(4-Cyclopropylpiperazin-1-yl)-5-pyrrolidin-1-ylmethylbenzooxazoleAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-cyclopropylpiperazin-1-yl)benzooxazole-5-carboxaldehyde (400 mg, 1.48 mmol) and pyrrolidine (210 mg, 2.96 mmol) in CH3OH/THF (36 mL, 1:3) was added acetic acid (142 mg, 2.37 mmol), followed by NaCNBH3 (137 mg, 2.37 mmol). The mixture was heated at reflux for 12 h. The volatiles were removed and the residue was diluted with water (5 mL). The resulting mixture was extracted with CH2Cl2 (3×10 mL) and the combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by column chromatography on silica gel (elute: 2% dichloromethane in methanol) to give 193 mg (40%) of 2-(4-cyclopropylpiperazin-1-yl)-5-pyrrolidin-1-ylmethylbenzooxazole.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 h
  3. customThe volatiles were removed
  4. additionthe residue was diluted with water (5 mL)
  5. extractionThe resulting mixture was extracted with CH2Cl2 (3×10 mL)
  6. dry with materialthe combined organic extracts were dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (elute: 2% dichloromethane in methanol)

Quellen und Nachweise

ORD-Eintrag
ord-72e341f6e5734187a26d1bd0b3729755
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772285B2

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