Sodium Hydroxide → HCID 178484203, compound

HRID 1922466Notes

Reaction equation

HRID 1922466 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:25][C:26]([C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)=[NH:27])[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH2:13][N:14](C)[C:15](=O)OC1C=CC=CC=1)[CH2:9][CH2:8][CH2:7]2.[OH-].[Na+]>C(O)C.O>[F:1][C:2]1[CH:3]=[C:4]([NH:25][C:26]([C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)=[NH:27])[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH2:13][NH:14][CH3:15])[CH2:9][CH2:8][CH2:7]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178484205HCID 178484205, compound

Product 1

HCID 178484203HCID 178484203, compoundYield 22.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of phenyl 2-(8-fluoro-6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate (400 mg, 0.884 mmol) in Ethanol (11 ml) was added sodium hydroxide (354 mg, 8.84 mmol) as a solution in Water (5.5 ml). The resulting mixture was stirred at reflux and monitored by TLC. After 3 h, the reaction mixture showed some formation of product, and some starting material. Due to the formation of some side product, the reaction was stopped, diluted with water and extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated, then chromatographed in 0-10% (2M NH3 in MeOH) in dichloromethane, giving the desired N-(8-fluoro-1-(2-(methylamino)ethyl)-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamide (67 mg, 0.202 mmol, 22.80% yield).1NMR (DMSO-d6) δ 7.71 (d, J=3, 1H); 7.58 (d, J=5 Hz, 1H); 7.07 (dd, J=5 Hz, 3 Hz, 1H); 6.48-6.43 (m, 2H); 6.41 (brd, J=15 Hz, 1H); 6.34 (s, 1H); 3.09 (m, 4H); 2.73-2.64 (m, 4H); 2.31 (s, 3H); 1.77-1.72 (m, 2H). EI-MS (m/z, %): 332 (M+, 9), 288 (100).

Workup

  1. temperatureat reflux
  2. extractionextracted with dichloromethane (3×)
  3. customThe combined organics were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed in 0-10% (2M NH3 in MeOH) in dichloromethane

Sources & evidence

ORD record
ord-0273bb67559648668727ff0c9d6e4ddd
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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