Cyanoacetic acid → 3-(4-{3-[7-(1-methyl-cyclohexanecarbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazin-1-yl)-3-oxo-propionitrile

HRID 1677482ノート

反応式

HRID 1677482 の反応式
[CH3:1][C:2]1([C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N:25]5[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]5)[CH:20]=4)[N:17]=3)[NH:12][CH:11]=2)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.N1(O)C2C=CC=CC=2N=N1.[C:41]([CH2:43][C:44](O)=[O:45])#[N:42].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH3:1][C:2]1([C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:20]=[C:21]([N:25]5[CH2:30][CH2:29][N:28]([C:44](=[O:45])[CH2:43][C:41]#[N:42])[CH2:27][CH2:26]5)[CH:22]=[CH:23][CH:24]=4)[N:17]=3)[NH:12][CH:11]=2)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

参加物

6

反応物 4

HCID 9740Cyanoacetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59540704(1-methyl-cyclohexyl)-[2-(3-piperazin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone

生成物 1

HCID 595408163-(4-{3-[7-(1-methyl-cyclohexanecarbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazin-1-yl)-3-oxo-propionitrile収率 56.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (1-methyl-cyclohexyl)-[2-(3-piperazin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone (130 mg, 0.32 mmol), benzotriazol-1-ol (52 mg, 0.38 mmol), cyano-acetic acid (74 mg, 0.39 mmol), and 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide hydrochloride (74 mg, 0.39 mmol), in DCM (35 ml), was treated with TEA (0.13 ml, 0.97 mmol). After stirring at room temperature for 16 hours, the reaction mixture was partitioned between DCM and water. The organic layers were collected, dried over MgSO4, filtered, and concentrated. Trituration of the resulting solid with 1:1 Et2O/Hex provided 85 mg (56%) of 3-(4-{3-[7-(1-methyl-cyclohexanecarbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazin-1-yl)-3-oxo-propionitrile as an off white solid. MP 214-216° C., M+H=471.

後処理

  1. customthe reaction mixture was partitioned between DCM and water
  2. customThe organic layers were collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-36be92e3caa44dc7ae7c8f2fa20c97b7
出典データセット
uspto-grants-2011_08
特許番号
US08008298B2

反応ノート

読み込み中…