Dimethylformamide → HCID 22936877, compound

HRID 1433732Notes

Reaction equation

[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([OH:22])=[C:17]([C:20]#[N:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[NH:23][C:24]([NH:26][CH:27]1[CH2:29][CH2:28]1)=[O:25].Cl.Cl[CH2:32][CH2:33][CH2:34][N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.O>[C:20]([C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][C:16]=1[O:22][CH2:32][CH2:33][CH2:34][N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1)[N:13]=[CH:12][CH:11]=[C:10]2[O:9][C:6]1[CH:5]=[CH:4][C:3]([NH:23][C:24]([NH:26][CH:27]2[CH2:28][CH2:29]2)=[O:25])=[C:2]([CH3:1])[C:7]=1[CH3:8])#[N:21]

Participants

Conditions

Temperature: 60 °C

Procedure

After adding the N-[2,3-dimethyl-4-(6-cyano-7-hydroxyquinolin-4-yloxy)phenyl]-N′-cyclopropylurea (100 mg) synthesized in Example 721, 1-(3-chloropropyl)pyrrolidine hydrochloride (95 mg) and potassium carbonate (150 mg) to dimethylformamide (2 ml), the mixture was heated at 60° C. for 7 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate, and then the organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was washed with ethyl acetate to obtain the title compound (49 mg) as light yellow crystals.

Workup

washthe organic layer was washed with water and saturated brine in that order
dry with materialdried over anhydrous sodium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe obtained crude product
washwas washed with ethyl acetate

Sources & evidence

ORD record: ord-46cb687fc13b499caedddc463232c4bd
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612092B2

Reaction notes

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