Phenyl 2-(6-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate → Phenyl methyl(2-(2-oxo-6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate

HRID 1922413Notes

Reaction equation

HRID 1922413 reaction equation
I.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](SC)=[NH:8].[NH2:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]([CH2:22][CH2:23][N:24]([CH3:34])[C:25](=[O:33])[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:17](=[O:35])[CH2:16][CH2:15]2>C(O)C>[CH3:34][N:24]([CH2:23][CH2:22][N:18]1[C:19]2[C:14](=[CH:13][C:12]([NH:11][C:7]([C:3]3[S:2][CH:6]=[CH:5][CH:4]=3)=[NH:8])=[CH:21][CH:20]=2)[CH2:15][CH2:16][C:17]1=[O:35])[C:25](=[O:33])[O:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 59807067Phenyl 2-(6-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamateHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178484234Phenyl methyl(2-(2-oxo-6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl thiophene-2-carbimidothioate hydroiodide (1.62 g, 5.71 mmol) was weighed into a round bottom flask with a stirbar. Phenyl 2-(6-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate (0.969 g, 2.85 mmol) was dissolved in ethanol (50 mL) and added to the flask. The resulting suspension was stirred overnight at room temperature. When the reaction was finished, argon was bubbled through the reaction mixture for 1 h, then the mixture was neutralized with sodium carbonate (sat. aq. solution). The product was extracted with dichloromethane (3×). The combined organics were dried over sodium sulfate, filtered and concentrated. The residue was chromatographed in (1:1) ethyl acetate:CH2Cl2 then 10% (2M NH3 in methanol) in dichloromethane. Yield: 700 mg, 55%. 1H NMR (DMSO-d6) δ 7.91 (m, 2H), 7.38 (m, 2H), 7.26 (m, 3H), 7.04 (m, 4H), 4.23 and 4.14 (2m, 2H), 3.63 and 3.51 (2m, 2H), 3.06 and 2.92 (2s, 3H), 2.84 (t, 2H, J=6.9 Hz), 2.56 (t, 2H, J=6.9 Hz); ESI-MS (m/z, %): 449 (MH+, 100).

Workup

  1. additionadded to the flask
  2. customargon was bubbled through the reaction mixture for 1 h
  3. extractionThe product was extracted with dichloromethane (3×)
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed in (1:1) ethyl acetate

Sources & evidence

ORD record
ord-7bad77fb50fa49fca69a91862769f2d6
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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