Water → HCID 22936564, compound

HRID 853264Notes

Reaction equation

HRID 853264 reaction equation
[Na].[C:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[OH:14])[N:10]=[CH:9][CH:8]=[C:7]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[O:24])=[C:18]([F:33])[CH:17]=1)#[N:3].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:42][CH:43]1[CH2:48][CH2:47][CH2:46][N:45]([CH3:49])[CH2:44]1.O>CN(C)C=O>[C:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH2:42][CH:43]1[CH2:48][CH2:47][CH2:46][N:45]([CH3:49])[CH2:44]1)[N:10]=[CH:9][CH:8]=[C:7]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[O:24])=[C:18]([F:33])[CH:17]=1)#[N:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1066903-Chloromethyl-1-methylpiperidinium chlorideHCID 136331047HCID 136331047, compound

Product 1

HCID 22936564HCID 22936564, compoundYield 3.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After dissolving 6-cyano-4-(4-(4-fluoroanilinocarbonyl)amino-3-fluorophenoxy)quinolin-7-ol sodium salt (222 mg), potassium carbonate (162 mg) and 3-chloromethyl-1-methylpiperidine hydrochloride (86 mg) in dimethylformamide (1.7 ml) and stirring the mixture overnight at 70–80° C., water was added, and extraction was performed with a tetrahydrofuran and ethyl acetate mixed solvent prior to concentration under reduced pressure and purification of the residue with NH Silica (Fuji Silysia Chemical). The obtained solid was washed with ether and dried to obtain the title compound (10 mg).

Workup

  1. extractionextraction
  2. concentrationto concentration
  3. customunder reduced pressure and purification of the residue with NH Silica (Fuji Silysia Chemical)
  4. washThe obtained solid was washed with ether
  5. customdried

Sources & evidence

ORD record
ord-57a1d827f39d402aacc01fad91918155
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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