Hydrochloric Acid → HCID 12133218, compound

HRID 1760568Notes

Reaction equation

HRID 1760568 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[N:22]=[C:21]([O:26]C)[CH:20]=[C:19]3[C:28]2[S:29][C:30]([CH3:33])=[CH:31][CH:32]=2)([C:10]2[N:11]([CH3:15])[CH:12]=[N:13][CH:14]=2)[OH:9])=[CH:4][CH:3]=1.Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:9])([C:10]2[N:11]([CH3:15])[CH:12]=[N:13][CH:14]=2)[C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[NH:22][C:21](=[O:26])[CH:20]=[C:19]3[C:28]2[S:29][C:30]([CH3:33])=[CH:31][CH:32]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10005176HCID 10005176, compound

Product 1

HCID 12133218HCID 12133218, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (4-Chloro-phenyl)-[2-methoxy-4-(5-methyl-thiophen-2-yl)-quinolin-6-yl]-(3-methyl-3H-imidazol-4-yl)-methanol (0.137 g, 0.288 mmol) in THF (3.2 ml) was added concentrated hydrogen chloride (HCl, 0.314 ml) dropwise. The mixture was heated at 60° C. for 24 hours. After cooling to room temperature, THF was removed. The aqueous solution was adjusted to pH=˜9 with 40% aqueous NaOH. The yellow solid was precipitated out. After filtration and washed with ethylacetae obtained 6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(5-methyl-thiophen-2-yl)-1H-quinolin-2-one (0.115 g, 0.248 mmol, 86%yield).

Workup

  1. temperatureAfter cooling to room temperature
  2. customTHF was removed
  3. customThe yellow solid was precipitated out
  4. filtrationAfter filtration
  5. washwashed with ethylacetae

Sources & evidence

ORD record
ord-38476398a1924c3aa72a59a068894cbe
Source dataset
uspto-grants-2005_01
Patent number
US06844357B2

Reaction notes

Loading…