Sodium Hydroxide → HCID 178484233, compound

HRID 1922414Notes

Reaction equation

HRID 1922414 reaction equation
[CH3:1][N:2]([CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:25]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[NH:26])=[CH:21][CH:22]=2)[CH2:17][CH2:16][C:15]1=[O:32])C(=O)OC1C=CC=CC=1.[OH-].[Na+]>CCO.O>[CH3:1][NH:2][CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:25]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[NH:26])=[CH:21][CH:22]=2)[CH2:17][CH2:16][C:15]1=[O:32]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178484234Phenyl methyl(2-(2-oxo-6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate

Product 1

HCID 178484233HCID 178484233, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Phenyl methyl(2-(2-oxo-6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate (700 mg, 1.56 mmol) was stirred in EtOH (20 mL). To this suspension was added solid NaOH (624 mg, 15.6 mmol), followed by water (10 mL). The flask was then fitted with a condenser and was heated to reflux for 2 h. When TLC analysis showed that the reaction was complete, the mixture was cooled to room temperature and diluted with water. The product was extracted with dichloromethane (3×) and the combined organics were dried, filtered and concentrated, then chromatographed in EtOAc, followed by 10% 2M NH3/MeOH in dichloromethane. The isolated spot was then triturated with methanol and ether. Yield (223 mg, 43%). 1H NMR (DMSO-d6) δ 7.73 (d, 1H, J=3.6 Hz), 7.59 (d, 1H, J=5.4 Hz), 7.10 (m, 2H), 6.73 (m, 2H), 6.45 (brs, 2H), 3.91 (t, 1H, J=7.2 Hz), 2.81 (t, 1H, J=7.2 Hz), 2.65 (t, 1H, J=7.2 Hz), 2.50 (t, 1H, J=7.2 Hz); ESI-MS (m/z, %): 329 (MH+, 70), 149 (100), 141 (80), 127 (96).

Workup

  1. customThe flask was then fitted with a condenser
  2. temperaturewas heated
  3. temperatureto reflux for 2 h
  4. extractionThe product was extracted with dichloromethane (3×)
  5. customthe combined organics were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed in EtOAc
  9. customThe isolated spot was then triturated with methanol and ether
  10. customYield (223 mg, 43%)

Sources & evidence

ORD record
ord-8eeb00cb81614f3a8408e6d33bb8da0b
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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