6-Amino-1-(2-(dimethylamino)ethyl)-8-fluoro-3,4-dihydroquinolin-2(1H)-one → HCID 178483723, compound

HRID 1922433Notes

Reaction equation

HRID 1922433 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[N:8]([CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[C:7](=[O:18])[CH2:6][CH2:5]2.I.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25](SC)=[NH:26]>C(O)C.O.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:17][N:15]([CH3:16])[CH2:14][CH2:13][N:8]1[C:9]2[C:4](=[CH:3][C:2]([NH:1][C:25]([C:21]3[S:20][CH:24]=[CH:23][CH:22]=3)=[NH:26])=[CH:11][C:10]=2[F:12])[CH2:5][CH2:6][C:7]1=[O:18]

Participants

6

Reactant 2

HCID 533921846-Amino-1-(2-(dimethylamino)ethyl)-8-fluoro-3,4-dihydroquinolin-2(1H)-oneHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178483723HCID 178483723, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

6-Amino-1-(2-(dimethylamino)ethyl)-8-fluoro-3,4-dihydroquinolin-2(1H)-one (312 mg, 1.24 mmol) was stirred to dissolve in ethanol (15 mL). To this solution was added methyl thiophene-2-carbimidothioate hydroiodide (708 mg, 2.48 mmol). The resulting suspension was stirred for 2 days 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 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: 27 mg). 1H NMR (DMSO-d6) δ 2.14 (s, 6H), 2.44 (t, 2H, J=6.7 Hz), 2.49 (m, 2H, masked by DMSO peak), 2.80 (t, 2H, J=6.6 Hz), 3.95 (t, 2H, J=6.5 Hz), 6.61 (m, 4H), 7.09 (m, 1H), 7.62 (m, 1H), 7.75 (m, 1H). ESI-MS: 361 (MH+, 100), 316 (40), 158.6 (57), 136 (37).

Workup

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

Sources & evidence

ORD record
ord-e003d4fd2bc94d7a8ced8fa5dbedc458
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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