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Methyl iodide → 5-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(methoxymethyl)pyridin-2-yl]amino}thiophene-3-carboxamide

HRID 385871
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HRID 385871 반응식
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([C:10]([OH:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[C:14]1[S:18][C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][OH:27])[N:21]=2)=[C:16]([C:28]([NH2:30])=[O:29])[CH:15]=1.I[CH3:32]>CN(C=O)C>[F:3][C:4]1[CH:9]=[C:8]([C:10]([OH:13])([CH3:11])[CH3:12])[CH:7]=[CH:6][C:5]=1[C:14]1[S:18][C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][O:27][CH3:32])[N:21]=2)=[C:16]([C:28]([NH2:30])=[O:29])[CH:15]=1
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참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 251234855-(2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl)-2-((6-(hydroxymethyl)-2-pyridinyl)amino)-3-thiophenecarboxamide

생성물 1

HCID 595259365-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(methoxymethyl)pyridin-2-yl]amino}thiophene-3-carboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

실험 절차

To a suspension of NaH (9.96 mg, 0.25 mmol) in DMF (1.25 mL) at 0° C. under argon was added 5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(hydroxymethyl)pyridin-2-yl]amino}thiophene-3-carboxamide (Example 43) (50 mg, 0.125 mmol) and the mixture was stirred for 20 minutes. Iodomethane (26.6 mg, 0.187 mmol) was then added and the reaction was allowed to warm to room temperature and subsequently heated to 60° C. overnight. The reaction was cooled to ambient temperature, quenched by the addition of water, extracted with ethyl acetate and concentrated in vacuo. The crude residue was reverse phase HPLC (acteonitrile/water with formic acid as a modifier) to afford the title compound.

후처리

  1. temperaturesubsequently heated to 60° C. overnight
  2. temperatureThe reaction was cooled to ambient temperature
  3. customquenched by the addition of water
  4. extractionextracted with ethyl acetate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-6b6b83f7c0fe4a7f93c55c4583e3ab21
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08367706B2

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