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

HRID 66385

反応式

HRID 66385 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b0197b5d3933400daa19b6d494d25eae
出典データセット
uspto-grants-1978_12
特許番号
US04131677

関連ノート

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