HCID 59807143, compound → HCID 178511879, compound

HRID 1922358Notes

Reaction equation

HRID 1922358 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][CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:7](=[O:21])[CH2:6][CH2:5]2.I.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[C:28](SC)=[NH:29]>C(O)C.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[N:15]1([CH2:14][CH2:13][CH2:12][N:8]2[C:9]3[C:4](=[CH:3][C:2]([NH:1][C:28]([C:24]4[S:23][CH:27]=[CH:26][CH:25]=4)=[NH:29])=[CH:11][CH:10]=3)[CH2:5][CH2:6][C:7]2=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

6

Reactant 2

HCID 59807143HCID 59807143, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178511879HCID 178511879, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 6-amino-1-(3-(piperidin-1-yl)propyl)-3,4-dihydroquinolin-2(1H)-one (0.065 g, 0.226 mmol) in dry ethanol (5 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.129 g, 0.452 mmol) at room temperature and the resulting mixture was stirred for 64 hours. The reaction was transferred to a separatory funnel and diluted with ethyl acetate (30 mL) and saturated sodium hydrogen carbonate (20 mL). The aqueous was partitioned twice more with ethyl acetate (2×20 mL). The combined organics were washed with brine and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2M ammonia in methanol:dichloromethane, 0-1:10-9). The product was dried under high vacuum. Yield: 46 mg of yellow solid (51%). 1H NMR (DMSO-d6) δ: 8.02 (d, J=3.9 Hz, 1H), 7.99 (d, J=3 Hz, 1H), 7.32 (d, J =4.8 Hz, 1H), 7.28 (d, J=6.3 Hz, 1H), 7.20 (s, 1H), 7.17 (s, 1H), 4.32 (br s, 2H), 3.98−3.93 (m, 2H), 3.45-3.40 (m, 4H), 3.16-3.10 (m, 4H), 2.95-2.90 (m, 4H), 2.61-2.56(m, 2H), 2.01-1.90 (m, 2H). MS (ESI): 397.2 (M+1). ESI-HRMS calculated for C22H29N4SO (MH+): 397.2056, Observed: 397.2073.

Workup

  1. customThe reaction was transferred to a separatory funnel
  2. customThe aqueous was partitioned twice more with ethyl acetate (2×20 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customSolvent was evaporated
  6. customcrude was purified by column chromatography (2M ammonia in methanol:dichloromethane, 0-1:10-9)
  7. customThe product was dried under high vacuum

Sources & evidence

ORD record
ord-34a137737081440e8fc3f7c7b3fe677d
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

Loading…