Cyclopropylamine → 5-(3-((cyclopropylamino)methyl)phenyl)-N-neopentylbenzo[d]isoxazol-3-amine

HRID 1011450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1011450
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[CH2:5]([NH:10][C:11]1[C:15]2[CH:16]=[C:17]([C:20]3[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=3)[CH:23]=O)[CH:18]=[CH:19][C:14]=2[O:13][N:12]=1)[C:6]([CH3:9])([CH3:8])[CH3:7].[H-].C(B)#N.[Na+].C(=O)([O-])O.[Na+]>C1COCC1>[CH:1]1([NH:4][CH2:23][C:22]2[CH:21]=[C:20]([C:17]3[CH:18]=[CH:19][C:14]4[O:13][N:12]=[C:11]([NH:10][CH2:5][C:6]([CH3:8])([CH3:7])[CH3:9])[C:15]=4[CH:16]=3)[CH:27]=[CH:26][CH:25]=2)[CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 119657963-(3-(Neopentylamino)benzo[d]isoxazol-5-yl)benzaldehyde2×HCID 178419206HCID 178419206, Verbindung

Produkt 1

HCID 119657955-(3-((cyclopropylamino)methyl)phenyl)-N-neopentylbenzo[d]isoxazol-3-amineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Cyclopropylamine (1.04 mL, 14.92 mmol, 5 equiv.) was added to a solution of 3-(3-(neopentylamino)benzo[d]isoxazol-5-yl)benzaldehyde (exemplary compound 52) (0.92 g, 2.98 mmol, 1 equiv.) in THF (50 mL) and sodium cyanoboran hydride (3.16 g, 14.92 mmol, 5 equiv.) was subsequently added to the mixture. The suspension was stirred for 3 days at RT, subsequently hydrolysed by the addition of sat. aq. sodium hydrogen carbonate sol. (approx. 5 mL) and the solvent removed in a vacuum. The residue was absorbed in EtOAc (10 mL) and extracted with sat. aq. sodium hydrogen carbonate sol. (2×15 mL) and sat. aq. NaCl solution (1×15 mL), dried (MgSO4) and the solvent removed in a vacuum. After column-chromatographic purification (EtOAc/MeOH; 20:1), the desired product (0.85 g, 82%) is obtained.

Aufarbeitung

  1. additionwas subsequently added to the mixture
  2. customthe solvent removed in a vacuum
  3. customThe residue was absorbed in EtOAc (10 mL)
  4. extractionextracted with sat. aq. sodium hydrogen carbonate sol. (2×15 mL) and sat. aq. NaCl solution (1×15 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in a vacuum
  7. customAfter column-chromatographic purification (EtOAc/MeOH; 20:1)

Quellen und Nachweise

ORD-Eintrag
ord-934a354159bb4383983963d842a72c3f
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977360B2

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