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

HRID 1922436노트

반응식

HRID 1922436 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

HCID 178483706HCID 178483706, 화합물

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 10340Sodium Carbonate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-50fb90103f884e3b83dd634effb5257f
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173813B2

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