HCID 53392183, compound → HCID 178480166, compound

HRID 1922372Notes

Reaction equation

HRID 1922372 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][CH:14]1[CH2:18][CH2:17][CH2:16][N:15]1[CH3:19])[C:7](=[O:20])[CH2:6][CH2:5]2.I.[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27](SC)=[NH:28]>C(O)C.C(OCC)C.CO.C(Cl)Cl>[CH3:19][N:15]1[CH2:16][CH2:17][CH2:18][CH:14]1[CH2:13][CH2:12][N:8]1[C:9]2[C:4](=[CH:3][C:2]([NH:1][C:27]([C:23]3[S:22][CH:26]=[CH:25][CH:24]=3)=[NH:28])=[CH:11][CH:10]=2)[CH2:5][CH2:6][C:7]1=[O:20]

Participants

6

Reactant 2

HCID 53392183HCID 53392183, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178480166HCID 178480166, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 6-amino-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-3,4-dihydroquinolin-2(1H)-one (1.15 g, 4.21 mmol) in absolute ethanol (25 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (2.40 g, 8.42 mmol) and stirred at room temperature for 18 hours. The reaction was diluted with diethyl ether (150 mL) and the precipitate collected by vacuum filtration. The precipitate was washed with ether (50 mL). The yellow solid was dissolved in water (50 mL) and transferred to a separatory funnel. The reaction was treated with 1N NaOH (10 mL) and extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to give a yellow oil which was subjected to flash chromatography on silica gel using 0-5% 2M NH3 in MeOH/CH2Cl2 to give a yellow foam. Yield: 1.11 g of yellow foam (69%). 1H-NMR (DMSO-d6) δ: 7.73 (d, J=3.0 Hz, 1H), 7.60 (d, J=5.4 Hz, 1H), 7.10-7.02 (m, 2H), 6.72-6.75 (m, 2H), 6.45 (br s, 2H), 3.91-3.80 (m, 2H), 2.96-2.90 (m, 1H), 2.82-2.78 (m, 2H), 2.19 (s, 3H), 2.08-1.80 (m, 6H), 1.66-1.49 (m, 4H).

Workup

  1. filtrationthe precipitate collected by vacuum filtration
  2. washThe precipitate was washed with ether (50 mL)
  3. dissolutionThe yellow solid was dissolved in water (50 mL)
  4. customtransferred to a separatory funnel
  5. additionThe reaction was treated with 1N NaOH (10 mL)
  6. extractionextracted with ethyl acetate (3×15 mL)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a yellow oil which
  12. customto give a yellow foam

Sources & evidence

ORD record
ord-62e1fdbcb0044712b243514981220ca9
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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