1-(2-(Dimethylamino)ethyl)-8-fluoro-1,2,3,4-tetrahydroquinolin-6-amine → HCID 178483706、化合物

HRID 1922436ノート

反応式

HRID 1922436 の反応式
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([NH2:16])=[CH:12][C:13]=2[F:15])[CH2:8][CH2:7][CH2:6]1.I.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](SC)=[NH:25]>C(O)C.O.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([NH:16][C:24]([C:20]3[S:19][CH:23]=[CH:22][CH:21]=3)=[NH:25])=[CH:12][C:13]=2[F:15])[CH2:8][CH2:7][CH2:6]1

参加物

6

反応物 2

HCID 533923481-(2-(Dimethylamino)ethyl)-8-fluoro-1,2,3,4-tetrahydroquinolin-6-amineHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

生成物 1

HCID 178483706HCID 178483706、化合物

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 10340Sodium Carbonate溶媒

実験手順

1-(2-(Dimethylamino)ethyl)-8-fluoro-1,2,3,4-tetrahydroquinolin-6-amine (222 mg, 0.935 mmol) was stirred to dissolve in ethanol in a round bottom flask. To this solution was added methyl thiophene-2-carbimidothioate hydroiodide (533 mg, 1.87 mmol). The resulting suspension was stirred overnight at room temperature. When TLC analysis showed that the reaction was finished, the mixture was diluted with water and aqueous sodium carbonate, then extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated and the crude product then chromatographed on silica gel using 0-10% (2M NH3 in MeOH) in ethyl acetate, then a second time using 20-80% MeCN in an aqueous buffer of ammonium carbonate and ammonium hydroxide adjusted to pH 10.6. Yield: 46 mg, 15%. 1H NMR (DMSO-d6) δ 1.75 (m, 2H), 2.16 (s, 6H), 2.46 (m, 2H), 2.66 (m, 2H), 3.12 (m, 4H), 6.40 (m, 4H), 7.07 (m, 1H), 7.57 (m, 1H), 7.71 (m, 1H). ESI-MS: 347 (MH+, 33), 276 (100), 143 (12).

後処理

  1. extractionextracted with dichloromethane (3×)
  2. customThe combined organics were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe crude product then chromatographed on silica gel using 0-10% (2M NH3 in MeOH) in ethyl acetate

出典と根拠

ORDレコード
ord-50fb90103f884e3b83dd634effb5257f
出典データセット
uspto-grants-2012_05
特許番号
US08173813B2

反応ノート

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