Iodoacetamide → 2-(3-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[2,3-b]pyridin-1-yl)acetamide

HRID 244394노트

반응식

HRID 244394 반응식
[F:1][C:2]([F:31])([F:30])[C:3]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[N:18]=[CH:17]2)([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)[OH:4].[OH-].[K+].I[CH2:35][C:36]([NH2:38])=[O:37]>CN(C=O)C.[Cl-].[NH4+]>[F:31][C:2]([F:1])([F:30])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:35][C:36]([NH2:38])=[O:37])[CH:6]=1)([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[N:18]=[CH:17]2)[OH:4]

참가 물질

6

반응물 3

HCID 3727IodoacetamideHCID 14797Potassium HydroxideHCID 249594552,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol

생성물 1

HCID 249594542-(3-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[2,3-b]pyridin-1-yl)acetamide수율 31%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 25517Ammonium Chloride용매

실험 절차

To a solution of 60 mg (0.14 mmol) of 2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol in 2 mL of DMF was added 21 mg (0.27 mmol) of powdered KOH followed by 51 mg (0.28 mmol) of iodoacetamide. The mixture stirred for 30 minutes, and was then diluted with saturated aqueous ammonium chloride and extracted with three 7 mL portions of ethyl acetate. The combined organic layers were washed with two 7 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel using dichloromethane to load the sample and then eluting with dichloromethane and then ethyl acetate. The material from the column was triturated with ether-hexanes and dried under house vacuum at 80° C. for 2 hours to afford 21 mg (30%) of the title compound. MS m/z 484.28 (MH+).

후처리

  1. extractionextracted with three 7 mL portions of ethyl acetate
  2. washThe combined organic layers were washed with two 7 mL portions of brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel
  7. washeluting with dichloromethane
  8. customThe material from the column was triturated with ether-hexanes
  9. customdried under house vacuum at 80° C. for 2 hours

출처 및 근거

ORD 기록
ord-d9fc076c680743b6951fb548ea3436bb
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658637B2

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