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

HRID 385874
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인쇄 미리보기

반응식

HRID 385874 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.Cl[CH2:32][C:33]1[O:34][C:35]([CH3:38])=[N:36][N:37]=1>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][C:33]3[O:34][C:35]([CH3:38])=[N:36][N:37]=3)[N:21]=2)=[C:16]([C:28]([NH2:30])=[O:29])[CH:15]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 38266202-(Chloromethyl)-5-methyl-1,3,4-oxadiazoleHCID 251234855-(2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl)-2-((6-(hydroxymethyl)-2-pyridinyl)amino)-3-thiophenecarboxamide

생성물 1

HCID 595260635-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-{[(5-methyl-1,3,4-oxadiazol-2-yl)methoxy]methyl}pyridin-2-yl)amino]thiophene-3-carboxamide

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

To a suspension of NaH (14 mg, 0.35 mmol) in DMF (1.75 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) (70 mg, 0.17 mmol) and the mixture was allowed to stir for 10 minutes. 2-(Chloromethyl)-5-methyl-1,3,4-oxadiazole (35 mg, 0.26 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-b15539a6a0534b5fa6f23f9dedf8e208
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08367706B2

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