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Lithium Hydroxide → 6-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]norbornane-2-carboxylic acid

HRID 527090
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HRID 527090 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15](S(C)=O)[C:14]([F:20])=[CH:13][N:12]=3)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.[NH2:31][CH:32]1[CH:37]2[CH2:38][CH:34]([CH2:35][CH:36]2[C:39]([OH:41])=[O:40])[CH2:33]1.C(N(C(C)C)CC)(C)C.[Li+].[OH-].FC(F)(F)C(O)=O>C1COCC1.CO>[F:20][C:14]1[C:15]([NH:31][CH:32]2[CH:37]3[CH2:38][CH:34]([CH2:35][CH:36]3[C:39]([OH:41])=[O:40])[CH2:33]2)=[N:16][C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([F:1])[CH:3]=3)[NH:8][CH:9]=2)=[N:12][CH:13]=1
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참가 물질

8

반응물 5

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 206527796-Aminobicyclo(2.2.1)heptane-2-carboxylic acid2회HCID 672853275-Fluoro-3-[5-fluoro-4-(methylsulfinyl)-2-pyrimidinyl]-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 67285046
6-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]norbornane-2-carboxylic acid

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

To a solution of 5-fluoro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine (0.187 g, 0.417 mmol) and 6-aminobicyclo-[2.2.1]heptane-2-carboxylic acid, 72h, (0.080 g, 0.417 mmol) in THF (3 mL) was added diisopropylethylamine (0.291 mL, 1.670 mmol). The reaction mixture was heated at 80° C. overnight. Aqueous LiOH (3 mL of 2M solution, 6.000 mmol) was added and the mixture was heated for another 7 hours. The mixture was diluted with MeOH, neutralized with trifluoroacetic acid, filtered and the resulting filrate was purified by preparatory HPLC chromatography to afford 50 mg of desired product.

후처리

  1. temperaturethe mixture was heated for another 7 hours
  2. filtrationfiltered
  3. customthe resulting filrate was purified by preparatory HPLC chromatography

출처 및 근거

ORD 기록
ord-4944e00922db42f4ba221226d9a10994
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09345708B2

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