HCID 57677472, compound → 3-[4-(4-Amino-2-fluorophenoxy)pyridin-2-yl]-1-methyl-1-(1-methylpiperidin-4-yl)urea

HRID 492835Notes

Reaction equation

HRID 492835 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C:25]([N:27]([CH3:35])[CH:28]3[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]3)=[O:26])[CH:19]=2)=[C:13]([F:36])[CH:12]=1)C1C=CC=CC=1.[H][H]>O1CCCC1.CO.[C].[Pd]>[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C:25](=[O:26])[N:27]([CH3:35])[CH:28]3[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]3)[CH:19]=2)=[C:13]([F:36])[CH:12]=1

Participants

6

Reactant 2

HCID 57677472HCID 57677472, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 231535663-[4-(4-Amino-2-fluorophenoxy)pyridin-2-yl]-1-methyl-1-(1-methylpiperidin-4-yl)ureaYield 100.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

After dissolving (3-fluoro-4-{2-[3-methyl-3-(1-methylpiperidin-4-yl)ureido]pyridin-4-yloxy}phenyl)carbamic acid benzyl ester (38.7 mg) in tetrahydrofuran (1.5 ml) and methanol (1.5 ml), 10% palladium-carbon (16 mg) was added under a nitrogen atmosphere. The atmosphere in the reaction vessel was replaced with hydrogen, and the mixture was stirred for 5 hours at room temperature. The catalyst was filtered and then washed with methanol. The filtrate was concentrated under reduced pressure to provide a crude product of the title compound as a pale yellow oil (28.5 mg).

Workup

  1. additionwas added under a nitrogen atmosphere
  2. filtrationThe catalyst was filtered
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-52e2bde64de44f4687edf14d5ac49bb5
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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