Triethylamine → HCID 22417798, compound

HRID 1720262Notes

Reaction equation

HRID 1720262 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:7]=[C:6]2[NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:22][CH:21]=1.[CH3:34][S:35]([Cl:38])(=[O:37])=[O:36].C(N(CC)CC)C>C1COCC1>[ClH:38].[CH:28]1([CH2:27][O:26][C:23]2[CH:22]=[CH:21][C:20]([NH:19][C:6]3[C:5]4[C:10](=[CH:11][CH:12]=[C:3]([NH:2][S:35]([CH3:34])(=[O:37])=[O:36])[CH:4]=4)[N:9]=[C:8]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:7]=3)=[CH:25][CH:24]=2)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67766224HCID 67766224, compound

Product 1

HCID 22417798HCID 22417798, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 6-amino-4-(p-cyclohexylmethoxyanilino) -2-phenylquinoline hydrochloride (0.21 g, 0.5 mmol) in anhydrous THF (10 ml) at 0° C. was added methanesulfonyl chloride (69 mg, 0.6 mmol) followed by addition of triethylamine (61 mg, 0.6 mmol). The reaction mixture was allowed to warm slowly to room temperature and stirred overnight. The solvent was removed by rotary evaporation and the residue partitioned between ethyl acetate (EtOAc) and 1M hydrochloric acid. The layers were separated, the organic layer was washed with saturated sodium bicarbonate and dried (Na2SO4) and the solvent was removed by rotary evaporation. The crude material was dissolved in warm methanol and treated with 1M HCl in ether. After 2 hours at room temperature, the solvent was removed by rotary evaporation and the residue recrystallized from methanol/ether to give 4-(p-cyclohexylmethoxyanilino)-6-methylsulfonamido-2-phenylquinoline hydrochloride (38%) as a pale yellow solid.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. customthe residue partitioned between ethyl acetate (EtOAc) and 1M hydrochloric acid
  3. customThe layers were separated
  4. washthe organic layer was washed with saturated sodium bicarbonate
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was removed by rotary evaporation
  7. dissolutionThe crude material was dissolved in warm methanol
  8. additiontreated with 1M HCl in ether
  9. waitAfter 2 hours at room temperature
  10. customthe solvent was removed by rotary evaporation
  11. customthe residue recrystallized from methanol/ether

Sources & evidence

ORD record
ord-301a097c282b44829f597809ddbb220a
Source dataset
uspto-grants-1996_04
Patent number
US05506235

Reaction notes

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