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

HRID 1257608ノート

反応式

HRID 1257608 の反応式
[C:1]([OH:6])(=O)[CH2:2][CH2:3][CH3:4].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:40][C:41]1[C:42]([NH:59][CH:60]2[CH2:65][CH2:64][N:63]([CH2:66][CH2:67][C:68]#[N:69])[CH2:62][CH2:61]2)=[C:43]2[CH:49]=[CH:48][N:47]([S:50]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)(=[O:52])=[O:51])[C:44]2=[N:45][CH:46]=1>CN(C=O)C.C(Cl)Cl>[C:53]1([S:50]([N:47]2[C:44]3=[N:45][CH:46]=[C:41]([NH:40][C:1](=[O:6])[CH2:2][CH2:3][CH3:4])[C:42]([NH:59][CH:60]4[CH2:61][CH2:62][N:63]([CH2:66][CH2:67][C:68]#[N:69])[CH2:64][CH2:65]4)=[C:43]3[CH:49]=[CH:48]2)(=[O:51])=[O:52])[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

参加物

7

反応物 4

HCID 264Butyric AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 673456183-[4-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidin-1-yl]-propionitrile

生成物 1

HCID 67348422N-{1-benzenesulfonyl-4-[1-(2-cyano-ethyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-butyramide

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

Butyric acid (0.029 ml, 0.321 mmol), diisopropylethylamine (0.065 ml, 0.375 mmol), and HATU (0.122 g, 0.321 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]-propionitrile (0.130 g, 0.306 mmol, prepared as described in Example 118) in a 4:1 mixture of CH2Cl2 and DMF (5 ml) at 25° C. The reaction mixture was stirred for 15 h at 25° C., then was partitioned between saturated NaHCO3 (6 ml) and CH2Cl2 (2 ml). The phases were separated using a phase separation column (Biotage) and the organic layer was concentrated under reduced pressure to give crude N-{1-benzenesulfonyl-4-[1-(2-cyano-ethyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-butyramide as a brown oil. LCMS (Method G, ESI): RT=0.59 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 (6 ml) and CH2Cl2 (2 ml)
  2. customThe phases were separated
  3. customa phase separation column (Biotage)
  4. concentrationthe organic layer was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-2401f59963674ec0b606610729d6b5c1
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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