N-bromobutanimide → HCID 76739665, compound

HRID 2189053Notes

Reaction equation

HRID 2189053 reaction equation
[C:1]([O:5][C:6](=[O:31])[CH2:7][O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([NH:15][C:16]2[C:17]3[CH:24]=[C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[O:22][C:18]=3[N:19]=[CH:20][N:21]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[Br:32]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:31])[CH2:7][O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([NH:15][C:16]2[C:17]3[C:24]([Br:32])=[C:23]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[O:22][C:18]=3[N:19]=[CH:20][N:21]=2)[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 76739682HCID 76739682, compound

Product 1

HCID 76739665HCID 76739665, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Suspend 1.65 g (3.9 mmol) of (+/−)-({3-[(6-phenylfuro[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}-oxy)acetic acid tert-butyl ester in 4 ml of carbon tetrachloride and add 762 mg (4.3 mmol) of N-bromosuccinimide. Heat the reaction mixture under reflux for 1 h. After cooling to RT, add a further 350 mg of N-bromosuccinimide. Stir the reaction mixture under reflux again for 1 h, then cool and concentrate under reduced pressure. From the residue, after purification by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 5:1), 0.99 g of the target product is isolated (50.6% of theory).

Workup

  1. temperatureHeat the reaction mixture
  2. temperatureunder reflux for 1 h
  3. temperatureunder reflux again for 1 h
  4. temperaturecool
  5. concentrationconcentrate under reduced pressure
  6. customFrom the residue, after purification by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-77816390becc44c8a25e3484abe1cb3f
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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