Dabco → 7-Benzyl-6-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile

HRID 902529ノート

反応式

HRID 902529 の反応式
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([C:15]#[N:16])=[C:11](Cl)[C:10]2[CH:18]=[CH:19][S:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:21]1([C:27]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)=[O:28])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C1N2CCN(CC2)C1.[Cl-].[NH4+]>CN(C=O)C>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([C:15]#[N:16])=[C:11]([N:24]2[CH2:25][CH2:26][N:21]([C:27]([C:29]3[S:30][CH:31]=[CH:32][CH:33]=3)=[O:28])[CH2:22][CH2:23]2)[C:10]2[CH:18]=[CH:19][S:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 9237DabcoHCID 25517Ammonium ChlorideHCID 7975621-(Thien-2-ylcarbonyl)piperazineHCID 693140757-Benzyl-4-chloro-6,7-dihydro-6-oxo-thieno[2,3-b]pyridine-5-carbonitrile

生成物 1

HCID 118526987-Benzyl-6-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile収率 29%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 7-benzyl-4-chloro-6,7-dihydro-6-oxo-thieno[2,3-b]pyridine-5-carbonitrile (64) (0.750 g, 0.0025 mol), piperazin-1-yl-thiophen-2-yl-methanone (0.69 g, 0.0035 mol), and DABCO (0.56 g, 0.005 mol) in anhydrous DMF was heated at 110° C. for 12 h. The solution was cooled and poured into a 5% ammonium chloride aqueous solution and the precipitated solid was collected by vacuum filtration. The solid was purified by reverse phase chromatography (MeCN/water) to yield 0.330 g (29%) of 7-benzyl-6-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile. MP 257° C.; 1H-NMR (DMSO-d6) δ 3.83 (m, 8H), 5.28 (s, 2H), 7.16 (m, 1H), 7.33 (m, 7H), 7.51 (d, J=3.2 Hz, 1H), 7.81 (d, J=4.8 Hz, 1H) ppm; EIMS m/z 461 (M+1).

後処理

  1. temperatureThe solution was cooled
  2. filtrationthe precipitated solid was collected by vacuum filtration
  3. customThe solid was purified by reverse phase chromatography (MeCN/water)

出典と根拠

ORDレコード
ord-abd06aa8f8bf4763873c57a9a97bd413
出典データセット
uspto-grants-2008_04
特許番号
US07365200B2

反応ノート

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