Hexane → HCID 23153183, compound

HRID 492732Notes

Reaction equation

HRID 492732 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-])=O)=[CH:19][C:18]=3[F:26])[N:13]=[CH:12][N:11]=2)C=CC=CC=1.[CH3:28][N:29]1[CH2:34][CH2:33][CH:32]([NH:35][CH3:36])[CH2:31][CH2:30]1.[H][H].CCCCCC>O1CCCC1.CO.C(OCC)C.[C].[Pd]>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][C:14]2[N:13]=[CH:12][N:11]=[C:10]([NH:9][C:8](=[O:27])[N:35]([CH3:36])[CH:32]3[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]3)[CH:15]=2)=[C:18]([F:26])[CH:19]=1

Participants

9

Reactant 4

HCID 8058HexaneHCID 5663231-Methyl-4-(methylamino)piperidineHCID 57677340HCID 57677340, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23153183HCID 23153183, compoundYield 45%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

[6-(2-Fluoro-4-nitrophenoxy)pyrimidin-4-yl]carbamic acid phenyl ester (200 mg) was dissolved in tetrahydrofuran (16 ml), and then 1-methyl-4-(methylamino)piperidine (0.236 ml) was added thereto while stirring, followed by stirring for 20 min. 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) in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a crude product (218 mg) of 3-[6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-yl]-1-methyl-1-(1-methylpiperidin-4-yl)urea. The crude product (218 mg) was dissolved in methanol (5 ml)-tetrahydrofuran (5 ml), and then 10% palladium carbon (115 mg) was added thereto under a nitrogen atmosphere, followed by replacing with hydrogen inside the system and stirring for 3 hrs. The reaction mixture was filtered to remove the catalyst, which was washed with ethanol. The filtrate was concentrated under a reduced pressure to give a residue, which was then suspended in diethyl ether (2 ml)-hexane (4 ml). The solid was filtered off and dried under aeration to provide the titled compound (91.0 mg, 45%) as yellow powder.

Workup

  1. stirringby stirring for 20 min
  2. customThe reaction mixture was partitioned between ethyl acetate (30 ml)
  3. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (20 ml), water (20 ml) and brine (20 ml) in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customto give a crude product (218 mg) of 3-[6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-yl]-1-methyl-1-(1-methylpiperidin-4-yl)urea
  7. stirringstirring for 3 hrs
  8. filtrationThe reaction mixture was filtered
  9. customto remove the catalyst, which
  10. washwas washed with ethanol
  11. concentrationThe filtrate was concentrated under a reduced pressure
  12. customto give a residue, which
  13. filtrationThe solid was filtered off
  14. customdried under aeration

Sources & evidence

ORD record
ord-5483b35a3247404da9974e673dd66b22
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

Loading…