Ethanol → 5-({7-[3-(Diethylamino)propoxy]-6-methoxy-4-quinolyl}sulfanyl)-2-thiopheneamine

HRID 1010244ノート

反応式

HRID 1010244 の反応式
[CH2:1]([N:3]([CH2:29][CH3:30])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([S:18][C:19]3[S:20][C:21]([N+:24]([O-])=O)=[CH:22][CH:23]=3)=[CH:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:27][CH3:28])[CH3:2].[Cl-].[NH4+].C(O)C>[Fe].O>[CH2:29]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([S:18][C:19]3[S:20][C:21]([NH2:24])=[CH:22][CH:23]=3)=[CH:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:27][CH3:28])[CH3:30]

参加物

6

反応物 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 58931471N,N-Diethyl-N-[3-((6-methoxy-4-[(5-nitro-2-thienyl)sulfanyl]-7-quinolyl)oxy)propyl]amine

生成物 1

HCID 589308085-({7-[3-(Diethylamino)propoxy]-6-methoxy-4-quinolyl}sulfanyl)-2-thiopheneamine収率 38.8%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

実験手順

N,N-Diethyl-N-[3-({6-methoxy-4-[(5-nitro-2-thienyl)sulfanyl]-7-quinolyl}oxy)propyl]amine (525 mg), iron powder (330 mg), ammonium chloride (660 mg), ethanol (20 ml) and water (5 ml) were stirred together at 80° C. for 80 minutes. After filtration with celite, NH type silica gel was added to the filtrate, the solvent was distilled off under reduced pressure and the reaction product was adsorbed onto the silica gel. The silica gel was charged into a dry column packed with NH type silica gel, and column purification was performed (ethyl acetate, followed by ethyl acetate:methanol=3:1) to obtain 190 mg of a brown oil.

後処理

  1. filtrationAfter filtration with celite, NH type silica gel
  2. additionwas added to the filtrate
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionThe silica gel was charged into a dry column
  5. custompacked with NH type silica gel, and column purification

出典と根拠

ORDレコード
ord-eb3107ba162345cc831871958a76248e
出典データセット
uspto-grants-2011_07
特許番号
US07973160B2

反応ノート

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