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Diisopropylethylamine → (2R)-4-{5-Fluoro-4-[4-(methylthio)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

HRID 468628
ノート
印刷プレビュー

反応式

HRID 468628 の反応式
C(N(CC)C(C)C)(C)C.[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:16][NH2:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:42][C:43]1[C:44]([C:61]2[CH:66]=[CH:65][C:64]([S:67][CH3:68])=[CH:63][CH:62]=2)=[CH:45][C:46](=[O:60])[N:47]([CH2:49][CH2:50][C@@:51]([CH3:59])([S:55]([CH3:58])(=[O:57])=[O:56])[C:52](O)=[O:53])[CH:48]=1>CN(C=O)C.CCOC(C)=O>[F:42][C:43]1[C:44]([C:61]2[CH:62]=[CH:63][C:64]([S:67][CH3:68])=[CH:65][CH:66]=2)=[CH:45][C:46](=[O:60])[N:47]([CH2:49][CH2:50][C@@:51]([CH3:59])([S:55]([CH3:58])(=[O:57])=[O:56])[C:52]([NH:17][O:16][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][O:10]2)=[O:53])[CH:48]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70664819(2R)-4-{5-Fluoro-4-[4-(methylthio)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanoic acid

生成物 1

HCID 86670639
(2R)-4-{5-Fluoro-4-[4-(methylthio)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide
収率 100%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

N,N-Diisopropylethylamine (450 uL, 2.45 mmol), O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (192 mg, 1.64 mmol) and HATU (447 mg, 1.23 mmol) were added to a solution of (2R)-4-{5-fluoro-4-[4-(methylthio)phenyl]-2-oxopyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanoic acid (339 mg, 0.82 mmol) in DMF (10 mL). The reaction was allowed to stir at rt for 18 h. The reaction mixture was diluted with EtOAc and washed with brine. The organics were dried (MgSO4), filtered and concentrated. The crude residue was purified via flash chromatography using a 40 g silica column and an eluent of EtOAc in n-heptane (0-100%) to afford the title compound (420 mg, 100%). MS (LCMS) m/z 511.4 (M−1).

後処理

  1. washwashed with brine
  2. dry with materialThe organics were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified via flash chromatography

出典と根拠

ORDレコード
ord-13e78e5c20694fe69333687fcc617f35
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08624034B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート