Sodium hydride → 5-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(2-methoxyethoxy) methyl]pyridin-2-yl}amino)thiophene-3-carboxamide

HRID 385873노트

반응식

HRID 385873 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.Br[CH2:32][CH2:33][O:34][CH3:35]>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][CH2:32][CH2:33][O:34][CH3:35])[N:21]=2)=[C:16]([C:28]([NH2:30])=[O:29])[CH:15]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 251234855-(2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl)-2-((6-(hydroxymethyl)-2-pyridinyl)amino)-3-thiophenecarboxamide

생성물 1

HCID 595257925-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(2-methoxyethoxy) methyl]pyridin-2-yl}amino)thiophene-3-carboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a suspension of NaH (7.5 mg, 0.19 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, 0.13 mmol) and the mixture was allowed to stir for 10 minutes. 1-Bromo-2-methoxyethane (26 mg, 0.187 mmol) was then added and the reaction was allowed to warm to room temperature overnight. The reaction was then 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. customThe reaction was then quenched by the addition of water
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-92db7a6066574ad2989834fe3ccc069d
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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