Hydrochloric Acid → HCID 118323983, compound

HRID 1778277Notes

Reaction equation

HRID 1778277 reaction equation
O.O.[Sn](Cl)Cl.Cl.[Cl:7][C:8]1[CH:9]=[C:10]([CH:39]=[CH:40][CH:41]=1)[CH2:11][CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)(O)[C:24]3[S:25][CH:26]=[CH:27][N:28]=3)[CH:21]=2)[N:16](C)[C:15](=[O:38])[CH:14]=1>CC(O)=O>[Cl:7][C:8]1[CH:9]=[C:10]([CH:39]=[CH:40][CH:41]=1)[CH2:11][CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH:23]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[C:24]3[S:25][CH:26]=[CH:27][N:28]=3)[CH:21]=2)[NH:16][C:15](=[O:38])[CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 118323986HCID 118323986, compound

Product 1

HCID 118323983HCID 118323983, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of tin(II) chloride dihydrate (121 mg, 0.536 mmol, 4 equip) and concentrated HCl (0.168 ml) in AcOH (4 ml) was added 4-(3-chlorophenethyl)-6-((4-chlorophenyl)(hydroxy)(thiazol-2-yl)methyl)-1-methylquinolin-2(1H)-one (68 mg, 0.134 mmol, 1 equip). The resulting solution was heated to 110° C. for 45 minutes. The reaction was cooled to room temperature and concentrated. The residue was taken up in dichloromethane, washed with saturated NaHCO3, dried (Na2SO4), and concentrated. The residue was purified by MPLC using dichloromethane-methanol as the eluent to yield a tacky, off-white solid. The solid was triturated repeatedly with ethyl ether to yield 4-(3-chlorophenethyl)-6-((4-chlorophenyl)(thiazol-2-yl)methyl)quinolin-2(1H)-one as a white solid.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated
  3. washwashed with saturated NaHCO3
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by MPLC
  7. customto yield a tacky, off-white solid
  8. customThe solid was triturated repeatedly with ethyl ether

Sources & evidence

ORD record
ord-edb07d67513d49c4b784038ea4eb81a1
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

Loading…