Acetic Acid → 5-[5-(Benzylamino-methyl)-pyridin-3-yl]-3-methyl-3H-benzooxazol-2-one

HRID 1253921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1253921
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([CH:17]=O)[CH:14]=[N:15][CH:16]=3)[CH:9]=[CH:10][C:5]=2[O:4][C:3]1=[O:19].[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:20]([NH:27][CH2:17][C:13]1[CH:12]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]3[O:4][C:3](=[O:19])[N:2]([CH3:1])[C:6]=3[CH:7]=2)[CH:16]=[N:15][CH:14]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866633595-(3-Methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-pyridine-3-carbaldehyde

Produkt 1

HCID 667979925-[5-(Benzylamino-methyl)-pyridin-3-yl]-3-methyl-3H-benzooxazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 5-(3-Methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-pyridine-3-carbaldehyde (100 mg, 0.39 mmol), Benzylamine (46.4 mg, 0.43 mmol), acetic acid (50 uL) and sodium triacetoxyborohydride (25 0 mg, 1.18 mmol) in CH2Cl2 (10 mL) was stirred at room temperature for 2 h. The mixture was quenched with NaHCO3 (saturated solution) and extracted with CH2Cl2 (20 mL×3). The combined extracts were washed with brine and dried over anhydrous Na2SO4. After filtration and concentration, the residue was obtained as yellow solid. ESI-MS m/z: 346.1 [M+1]+, Retention time 1.11 min.

Aufarbeitung

  1. customThe mixture was quenched with NaHCO3 (saturated solution)
  2. extractionextracted with CH2Cl2 (20 mL×3)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe residue was obtained as yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-a0908c60216246c391c83f5fe32a1f6c
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455522B2

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