4-Amino-1-methylpiperidine → HCID 23153271, compound

HRID 492832Notes

Reaction equation

HRID 492832 reaction equation
C1(O[C:8](=[O:27])[NH:9][C:10]2[CH:15]=[C:14]([O:16][C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=3[F:26])[N:13]=[CH:12][N:11]=2)C=CC=CC=1.[NH2:28][CH:29]1[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]1>CN(C)C=O>[F:26][C:18]1[CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=[CH:22][C:17]=1[O:16][C:14]1[N:13]=[CH:12][N:11]=[C:10]([NH:9][C:8]([NH:28][CH:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)=[O:27])[CH:15]=1

Participants

4

Reactant 2

HCID 27375314-Amino-1-methylpiperidineHCID 57677340HCID 57677340, compound

Product 1

HCID 23153271HCID 23153271, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

[6-(2-Fluoro-4-nitrophenoxy)pyrimidin-4-yl]carbamic acid phenyl ester (190 mg) was dissolved in N,N-dimethylformamide (2 ml), and then 4-amino-1-methylpiperidine (176 mg)-N,N-dimethylformamide (3 ml) was added thereto, followed by stirring for 4 hrs. The reaction mixture was partitioned between ethyl acetate (30 ml) and a saturated aqueous solution of sodium hydrogencarbonate (20 ml). The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (20 ml), water (20 ml) and brine (20 ml), and dried over anhydrous sodium sulfate. The solvent was evaporated to give a crude product of 1-[6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-yl]-3-(1-methylpiperidin-4-yl)urea (200 mg). The crude product (200 mg) was dissolved in methanol (5 ml)-tetrahydrofuran (5 ml), and then 10% palladium carbon (109 mg) was added thereto under a nitrogen atmosphere, followed by replacing with hydrogen inside the system and stirring overnight. After replacing with nitrogen inside the system, the catalyst was filtered, and washed with ethanol. The filtrate was concentrated under a reduced pressure to give a residue, to which diethyl ether (2.5 ml)-hexane (5.0 ml) was added to suspend. The solid was filtered off, and dried under aeration to provide a crude product of 1-[6-(4-amino-2-fluorophenoxy)pyrimidin-4-yl]-3-(1-methylpiperidin-4-yl)urea (183 mg).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (30 ml)
  2. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (20 ml), water (20 ml) and brine (20 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7cda5007bee043c681150c0dc9fe82dd
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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