Water → 8-Methyl-6-[2-(tetrahydropyran-2-yloxy)ethoxy]-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

HRID 657862

반응식

HRID 657862 반응식
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][OH:10].[H-].[Na+].Br.Cl[C:15]1[CH:16]=[C:17]([CH3:25])[C:18]2[N:19]([C:21]([NH2:24])=[N:22][N:23]=2)[N:20]=1.O>CN(C=O)C>[CH3:25][C:17]1[C:18]2[N:19]([C:21]([NH2:24])=[N:22][N:23]=2)[N:20]=[C:15]([O:10][CH2:9][CH2:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[CH:16]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 41668332-(Oxan-2-yloxy)ethan-1-olHCID 866507966-Chloro-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide

생성물 1

HCID 580460108-Methyl-6-[2-(tetrahydropyran-2-yloxy)ethoxy]-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
40 °C

실험 절차

2-(Tetrahydropyran-2-yloxy)ethanol (3.85 ml) was initially charged in DMF (25 ml), admixed under argon with sodium hydride (681 mg) and stirred at 40° C. for 0.5 h. Subsequently, 6-chloro-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide (W2.002; 1.5 g), dissolved in DMF (25 ml), was added dropwise. After 40 min, the mixture was admixed with water and extracted by shaking four times with dichloromethane. To eliminate the excess alcohol, the mixture was chromatographed first through a short silica gel column with MtB ether and then with 8:2 dichloromethane/methanol. The clean product fractions were combined and dried. 678 mg of the title compound were obtained.

후처리

  1. additionwas added dropwise
  2. waitAfter 40 min
  3. extractionextracted
  4. stirringby shaking four times with dichloromethane
  5. customthe mixture was chromatographed first through a short silica gel column with MtB ether
  6. customdried

출처 및 근거

ORD 기록
ord-53e71004c55345a8923e3d45c877db14
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076336B2

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