Pyridine → N-(5-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-ethylphenyl)pivalamide

HRID 539813노트

반응식

HRID 539813 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([CH2:18][CH3:19])=[C:15]([CH:17]=3)[NH2:16])[N:10]=2)[N:7]=1.C(#N)C.N1C=CC=CC=1.[CH3:29][C:30]([CH3:35])([CH3:34])[C:31](Cl)=[O:32]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([CH2:18][CH3:19])=[C:15]([NH:16][C:31](=[O:32])[C:30]([CH3:35])([CH3:34])[CH3:29])[CH:17]=3)[N:10]=2)[N:7]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 6342AcetonitrileHCID 62493Pivaloyl chlorideHCID 575162295-(6-Chloroimidazo[1,2-b]pyridazin-2-yl)-2-ethylaniline

생성물 1

HCID 86667863N-(5-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-ethylphenyl)pivalamide수율 92.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A flask is charged with 5-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-ethylaniline (4.00 g, 0.0146 mol), acetonitrile (120 mL) and pyridine (3.54 mL, 0.0438 mol). The mixture is stirred and trimethylacetyl chloride (1.98 mL, 0.0161 mol) is added and the mixture stirred for 16 hr at room temp. When the reaction is complete the mixture is diluted with water (500 mL) and stirred for 1 hour, and solid collected, washed with water (3×50 mL). Crude product is purified by silica gel chromatography (0-50% EtOAc in CH2Cl2) to give the title compound (4.8 g, 92%). LCMS m/z=357.5, 359.4 [M+H]+, tR=2.57 min.

후처리

  1. stirringthe mixture stirred for 16 hr at room temp
  2. stirringstirred for 1 hour
  3. customsolid collected
  4. washwashed with water (3×50 mL)
  5. customCrude product is purified by silica gel chromatography (0-50% EtOAc in CH2Cl2)

출처 및 근거

ORD 기록
ord-b80fc4985621432b8490cb217cb732aa
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871767B2

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