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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 75049
ノート
印刷プレビュー

反応式

HRID 75049 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 206527796-Aminobicyclo(2.2.1)heptane-2-carboxylic acid2 回HCID 672853275-Fluoro-3-[5-fluoro-4-(methylsulfinyl)-2-pyrimidinyl]-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine

生成物 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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

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 filtrate was purified by preparatory HPLC chromatography to afford 50 mg of desired product.

後処理

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

出典と根拠

ORDレコード
ord-086f6eb3d4f94ecb9d6ad9979dc47cb4
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08829007B2

反応ノート

読み込み中…

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