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

HRID 66385

Reaction equation

HRID 66385 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b0197b5d3933400daa19b6d494d25eae
Source dataset
uspto-grants-1978_12
Patent number
US04131677

Linked notes

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