4-Pyridinecarboxylic acid, 1-oxide → 1-(8-CHLORO-5,11-DIHYDRO[1]BENZOTHIEPINO[4,3-b]PYRIDIN-11-YL)-4-(4-PYRIDINYLCARBONYL)PIPERAZINE N4-OXIDE

HRID 1647255ノート

反応式

HRID 1647255 の反応式
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[CH:6]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:7]3[C:12]([CH2:13][S:14][C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3.[C:23](O)(=[O:31])[C:24]1[CH:29]=[CH:28][N+:27]([O-])=[CH:26][CH:25]=1.O.[OH:34]N1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>ClCCl>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[CH:6]([N:15]3[CH2:16][CH2:17][N+:18]([O-:34])([C:23]([C:24]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)=[O:31])[CH2:19][CH2:20]3)[C:7]3[C:12]([CH2:13][S:14][C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3

参加物

6

反応物 4

HCID 261304-Pyridinecarboxylic acid, 1-oxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 157805018-Chloro-5,11-dihydro-11-(1-piperazinyl)[1]benzothiepino[4,3-b]pyridine

生成物 1

HCID 867487601-(8-CHLORO-5,11-DIHYDRO[1]BENZOTHIEPINO[4,3-b]PYRIDIN-11-YL)-4-(4-PYRIDINYLCARBONYL)PIPERAZINE N4-OXIDE

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred suspension of 8-chloro-5,11-dihydro-11-(1-piperazinyl)[1]benzothiepino[4,3-b]pyridine (251 mg, 0.762 mmol) and isonicotinic acid N-oxide (128 mg, 0.918 mmol) in dry dichloromethane (20 mL), add 1-hydroxybenzotriazole hydrate (123 mg, 0.909 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (175 mg, 0.912 mmol). Stir the resultant mixture at room temperature for 3 hours. Wash the reaction mixture successively with 2.5M aqueous sodium hydroxide (5 mL), water (4×10 mL), and brine (15 mL). Dry the washed solution over anhydrous magnesium sulfate, filter out the drying agent, and remove solvent from the filtrate under reduced pressure. Flash chromatograph the residue on silica gel, eluting with methanol/dichloromethane (1:9) to obtain the title compound as a 3/4 hydrate (240 mg, 70% yield): mp 162°-165.5° C. (melts to a viscous gum); MS (FAB) m/z 450 [M+ +1].

後処理

  1. washWash the reaction mixture successively with 2.5M aqueous sodium hydroxide (5 mL), water (4×10 mL), and brine (15 mL)
  2. dry with materialDry the washed solution over anhydrous magnesium sulfate
  3. filtrationfilter out the drying agent
  4. customremove solvent from the filtrate under reduced pressure
  5. washFlash chromatograph the residue on silica gel, eluting with methanol/dichloromethane (1:9)

出典と根拠

ORDレコード
ord-1bbe4de8b91442fc8c9b2c079b031bd0
出典データセット
uspto-grants-1995_07
特許番号
US05430032

反応ノート

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