Hydrochloric Acid → HCID 67374073、化合物

HRID 1972001ノート

反応式

HRID 1972001 の反応式
[CH2:1]([C:5]1[N:6]=[N:7][C:8]([O:27][CH:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[C:13]([N+:24]([O-])=O)[CH:12]=1)[CH2:2][CH2:3][CH3:4].[ClH:35]>C(O)(=O)C.O.CCOC(C)=O.C([O-])(O)=O.[Na+].C(Cl)Cl.CCOCC.[Fe]>[ClH:35].[ClH:35].[ClH:35].[CH2:1]([C:5]1[N:6]=[N:7][C:8]([O:27][CH:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[C:13]([NH2:24])[CH:12]=1)[CH2:2][CH2:3][CH3:4]

参加物

9

反応物 2

HCID 313Hydrochloric AcidHCID 67371453HCID 67371453、化合物

生成物 1

HCID 67374073HCID 67374073、化合物

試薬・触媒・溶媒 6

HCID 23925Iron触媒HCID 176Acetic Acid溶媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒HCID 22728543Water ethylacetate溶媒

反応条件

温度
100 °C

実験手順

To a solution of 3-butyl-4-(4-cyclohexyloxy-3-nitro-phenyl)-6-(1-methyl-piperidin-4-yloxy)-pyridazine (5 mmol, 2.34 g) in acetic acid (10 mL) was added iron powder (˜325 mesh, 50 mmol, 2.80 g). And the mixture was stirred at 100° C. for 0.5 hour. It was then diluted with water/EtOAc and neutralized slowly with NaHCO3 powder. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (DCM to DCM+10% 2N NH3 in MeOH) to give a colorless sticky solid, which was dissolved in DCM (10 mL), 2N HCl in ether (10 mL) was added, kept at room temperature for 10 min, condensed, triturated with hexanes to provide 5-[3-butyl-6-(1-methyl-piperidin-4-yloxy)-pyridazin-4-yl]-2-cyclohexyloxy-phenylamine trihydrochloride (2.06 g).

後処理

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography (DCM to DCM+10% 2N NH3 in MeOH)
  3. customto give a colorless sticky solid, which
  4. waitkept at room temperature for 10 min
  5. customcondensed
  6. customtriturated with hexanes

出典と根拠

ORDレコード
ord-8572489f319e45b999c23af1d94fd73d
出典データセット
uspto-grants-2013_04
特許番号
US08431575B2

反応ノート

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