(2,2-Diethoxyethyl)dimethylamine → 2-[3-(2-Dimethylaminoethyl)aminophenyl]oxazolo[4,5-b]pyridine

HRID 259573

Reaktionsgleichung

Reaktionsgleichung von HRID 259573
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[C:11]([N:16]=2)=[N:12][CH:13]=[CH:14][CH:15]=3)[CH:5]=[CH:6][CH:7]=1.[CH3:17][N:18]([CH2:20][CH:21]=O)[CH3:19].C(OC(OCC)CN(C)C)C.[BH4-].[Na+]>O.C(O)C>[CH3:17][N:18]([CH3:19])[CH2:20][CH2:21][NH:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[C:11]([N:16]=2)=[N:12][CH:13]=[CH:14][CH:15]=3)[CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 77163(2,2-Diethoxyethyl)dimethylamineHCID 6110863-(Oxazolo[4,5-b]pyridin-2-yl)anilineHCID 4311764Sodium borohydrideHCID 101976222-(Dimethylamino)acetaldehyde

Produkt 1

HCID 227547812-[3-(2-Dimethylaminoethyl)aminophenyl]oxazolo[4,5-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1.1 g., (0.005 mole) of 2-(3-aminophenyl)oxazolo[4,5-b]pyridine and 50 ml. of ethanol is reacted with dimethylaminoacetaldehyde [from 0.96 g. (0.006 mole) dimethylaminoacetaldehyde diethylacetal]by gentle heating to complete the intermediate Schiff base formation. The mixture is then cooled and 60 mg., (0.0015 mole) of sodium borohydride is added, and the mixture allowed to stir overnight at room temperature. Water is added, the solvents are removed in vacuo, and the residue is distributed between water and methylene chloride. The organic layer is dried and concentrated in vacuo to give crude 2-[3-(2-dimethylaminoethyl)aminophenyl]oxazolo[4,5-b]pyridine, purified via column chromatography using an alumina column with an ethylacetate-ether mixture (v/v 0-60% ethylacetate) as eluant.

Aufarbeitung

  1. additionA mixture of 1.1 g
  2. temperatureby gentle heating
  3. temperatureThe mixture is then cooled
  4. customthe solvents are removed in vacuo
  5. customThe organic layer is dried
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-54eb32033ce94b128bd5f8bee5637b0c
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04038396

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