Acetonitrile → N-[5-(6-chloroimidazo[1,2-a]pyridin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide

HRID 539757노트

반응식

HRID 539757 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]([C:18]([F:21])([F:20])[F:19])=[C:15]([CH:17]=3)[NH2:16])[N:10]=2)[CH:7]=1.C(#N)C.[CH3:25][C:26]([CH3:31])([CH3:30])[C:27](Cl)=[O:28]>N1C=CC=CC=1>[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]([C:18]([F:21])([F:20])[F:19])=[C:15]([NH:16][C:27](=[O:28])[C:26]([CH3:31])([CH3:30])[CH3:25])[CH:17]=3)[N:10]=2)[CH:7]=1

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 62493Pivaloyl chlorideHCID 575162705-(6-Chloroimidazo[1,2-a]pyridin-2-yl)-2-(trifluoromethyl)aniline

생성물 1

HCID 67983654N-[5-(6-chloroimidazo[1,2-a]pyridin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide수율 54%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
80 °C

실험 절차

A 20 mL vial is charged with 5-(6-chloroimidazo[1,2-a]pyridin-2-yl)-2-(trifluoromethyl)aniline (0.156 g, 0.5 mmol), acetonitrile (4.12 mL) and pyridine (0.081 mL). The mixture is added trimethylacetyl chloride (0.123 mL, 0.001 mol) and stirred for 20 min at 80° C. The solution is concentrated, taken into EtOAc (10 mL) and washed once with HCl (10 mL, 1M) and NaOH (10 mL, 1M). Organics are dried, concentrated purified on silica (0-100% EtOAc in Hexanes) to give the title compound (106 mg, 54% yield). LCMS m/z=396.4 [M+H]+, tR=2.54 min. (compound same as Example 81)

후처리

  1. concentrationThe solution is concentrated
  2. washwashed once with HCl (10 mL, 1M) and NaOH (10 mL, 1M)
  3. customOrganics are dried
  4. concentrationconcentrated
  5. custompurified on silica (0-100% EtOAc in Hexanes)

출처 및 근거

ORD 기록
ord-62f960e453e24034a49e762f45ecdbef
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871767B2

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