Hydrochloric Acid → HCID 86706570, compound

HRID 2174563Notes

Reaction equation

HRID 2174563 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:19])=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[C:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:27]=[C:28]([NH:31]C(=O)C)[S:29][CH:30]=2)=[CH:22][CH:21]=1.Cl>C(O)C>[ClH:1].[NH2:31][C:28]1[S:29][CH:30]=[C:26]([C:23]2[CH:24]=[CH:25][C:20]([C:3]3[CH:4]=[C:5]4[C:10](=[CH:11][C:2]=3[Cl:1])[NH:9][C:8](=[O:12])[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:6]4[OH:19])=[CH:21][CH:22]=2)[N:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 60198493HCID 60198493, compound

Product 1

HCID 86706570HCID 86706570, compoundYield 158%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-{4-[4-(7-chloro-4-hydroxy-2-oxo-3-phenyl-1,2-dihydro-6-quinolinyl)phenyl]-1,3-thiazol-2-yl}acetamide (Example 9) (1.7 g, 3.81 mmol) in ethanol (20 mL) was added concentrated hydrochloric acid (5.72 mL, 57.2 mmol) and the reaction mixture was stirred at 100° C. for 4 h. After cooling, the reaction mixture was filtered. The solid was washed with water and dried under reduced pressure to give the title compound 6-[4-(2-amino-1,3-thiazol-4-yl)phenyl]-7-chloro-4-hydroxy-3-phenylquinolin-2(1H)-one hydrochloride (1.45 g, 3.01 mmol, 79% yield) as a grey powder. LCMS: (M+H)+=446; Rt=2.44 min. HRMS calculated for C24H15ClN3O2S (M−H)+: 444.0574. found: 444.0532.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. washThe solid was washed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-53389097254f46bfb22b9a31e59aea00
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

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