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

HRID 259573

반응식

HRID 259573 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-54eb32033ce94b128bd5f8bee5637b0c
출처 데이터셋
uspto-grants-1977_07
특허 번호
US04038396

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