HCID 59807111, compound → HCID 178463987, compound

HRID 1922353Notes

Reaction equation

HRID 1922353 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]([CH2:18][CH3:19])[CH2:16][CH3:17])[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)(=O)C.C(=O)([O-])O.[Na+]>[CH2:16]([N:15]([CH2:18][CH3:19])[CH2:14][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])[CH3:17]

Participants

6

Reactant 2

HCID 59807111HCID 59807111, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178463987HCID 178463987, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 6-Amino-1-(3-diethylamino-propyl)-3,4-dihydro-1H-quinolin-2-one (0.058 g, 0.211 mmol) in dry ethanol (5 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.120 g, 0.421 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 7 was dried under high vacuum. Yield: 35 mg of yellow solid (44%). 1H NMR (CDCl3) δ: 7.44 (d, J=5.4 Hz, 1H), 7.41 (d, J=3.3 Hz, 1H), 7.09 (t, J=4.2 Hz, 1H), 7.06 (d, J=8.4 Hz, 1H), 6.88 (d, J=2.1 Hz, 1H), 6.84 (d, J=4.2 Hz, 1H), 4.90 (br s, 2H), 4.03-3.99 (m, 2H), 2.90-2.85 (m, 2H), 2.77-2.62 (m, 8H), 2.03-1.93 (m, 2H), 1.15 (t, J=7.2 Hz, 6H). MS (ESI): 385.2 (M+1). ESI-HRMS calculated for C21H29N4SO2 (MH+): 385.2056, Observed: 385.2040.

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. dry with materialThe product 7 was dried under high vacuum

Sources & evidence

ORD record
ord-75118440b7bd4633a48c05ab5e30820d
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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