Potassium Carbonate → HCID 22646558, compound

HRID 393617Notes

Reaction equation

Cl.Cl[CH2:3][C:4]1[N:5]=[C:6]([CH3:9])[S:7][CH:8]=1.[Cl:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([OH:23])=[C:18]([O:21][CH3:22])[CH:19]=2)[N:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH2:3][C:4]3[N:5]=[C:6]([CH3:9])[S:7][CH:8]=3)=[C:18]([O:21][CH3:22])[CH:19]=2)[N:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 70 °C

Procedure

4-Chloromethyl-2-methylthiazole hydrochloride (226 mg, 1.23 mmol) was added to a suspension of 4-chloro-7-hydroxy-6-methoxyquinoline (216 mg, 1 mmol), (prepared as described for the starting material in Example 3), and potassium carbonate (483 mg, 3.5 mmol) in DMF (10 ml). The mixture was stirred for 2.5 hours at 70° C. The volatiles were removed by evaporation and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), the insoluble materials were removed by filtration and the volatiles were removed by evaporation. The residue was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 4-chloro-6-methoxy-7-(2-methylthiazol-4-ylmethoxy)quinoline (352 mg, 55%).

Workup

custom(prepared
customThe volatiles were removed by evaporation
customthe residue was partitioned between ethyl acetate and water
washThe organic layer was washed with brine
dry with materialdried (MgSO4)
customthe insoluble materials were removed by filtration
customthe volatiles were removed by evaporation
customThe residue was triturated with ether
filtrationcollected by filtration
washwashed with ether
customdried under vacuum

Sources & evidence

ORD record: ord-63e3774a87244f3ebde2d9d85d78f287
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809097B1

Reaction notes

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