Propionic Acid → N-{1-benzenesulfonyl-4-[1-(2-cyano-1-methyl-ethyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-propionamide

HRID 1257615ノート

反応式

HRID 1257615 の反応式
[C:1]([OH:5])(=O)[CH2:2][CH3:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH2:39][C:40]1[C:41]([NH:58][CH:59]2[CH2:64][CH2:63][N:62]([CH:65]([CH3:69])[CH2:66][C:67]#[N:68])[CH2:61][CH2:60]2)=[C:42]2[CH:48]=[CH:47][N:46]([S:49]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)(=[O:51])=[O:50])[C:43]2=[N:44][CH:45]=1>CN(C=O)C.C(Cl)Cl>[C:52]1([S:49]([N:46]2[C:43]3=[N:44][CH:45]=[C:40]([NH:39][C:1](=[O:5])[CH2:2][CH3:3])[C:41]([NH:58][CH:59]4[CH2:60][CH2:61][N:62]([CH:65]([CH3:69])[CH2:66][C:67]#[N:68])[CH2:63][CH2:64]4)=[C:42]3[CH:48]=[CH:47]2)(=[O:50])=[O:51])[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

参加物

7

反応物 4

HCID 1032Propionic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 673436313-[4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidin-1-yl]-butyronitrile

生成物 1

HCID 67343906N-{1-benzenesulfonyl-4-[1-(2-cyano-1-methyl-ethyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-propionamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

Propionic acid (0.0176 ml, 0.320 mmol), HATU (0.122 g, 0.320 mmol), and diisopropylethylamine (0.062 ml, 0.358 mmol) were added sequentially to a solution of 3-[4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidin-1-yl]-butyronitrile (0.134 g, 0.305 mmol) in a 4:1 mixture of CH2Cl2 and DMF (5 ml) at 25° C. The reaction mixture was stirred for 14 h at 25° C., then was partitioned between saturated NaHCO3 (4 ml) and CH2Cl2 (3 ml). The phases were separated using a phase separator column (Biotage) and the organic layer was concentrated under reduced pressure to afford crude N-{1-benzenesulfonyl-4-[1-(2-cyano-1-methyl-ethyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-propionamide as a brown oil. LCMS (Method G, ESI): RT=0.60 min, m+H=495.3. This material was used in the next step below without additional purification or characterization.

後処理

  1. customwas partitioned between saturated NaHCO3 (4 ml) and CH2Cl2 (3 ml)
  2. customThe phases were separated
  3. concentrationthe organic layer was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-7da0bb9abd63467bbd0ab73a9ec81faf
出典データセット
uspto-grants-2013_06
特許番号
US08461328B2

反応ノート

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