Triethylamine → HCID 23153330, compound

HRID 492823Notes

Reaction equation

HRID 492823 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:29])[CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH2:27])[CH:22]=3)=[CH:16][C:15]=2[F:28])=[O:12])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:38](OC1C=CC=CC=1)=[O:39].[N:47]1([CH:53]2[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]2)[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:29])[CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:38]([N:56]4[CH2:57][CH2:58][CH:53]([N:47]5[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]5)[CH2:54][CH2:55]4)=[O:39])[CH:22]=3)=[CH:16][C:15]=2[F:28])=[O:12])=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 786071,4'-BipiperidineHCID 23152971HCID 23152971, compound

Product 1

HCID 23153330HCID 23153330, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(4-Fluorophenyl)-N′-[4-(2-aminopyridin-4-yloxy)-2-fluorophenyl]malonamide (17.0 mg) was dissolved in tetrahydrofuran (1.0 ml), and then triethylamine (0.015 ml) and phenyl chloroformate (0.013 ml) were added dropwise thereto under a nitrogen atmosphere at room temperature, followed by stirring for 30 min. The reaction mixture was concentrated under a reduced pressure to give a residue, which was then dissolved in N,N-dimethylformamide (0.5 ml). 4-(Piperidin-1-yl)piperidine (80 mg) was added thereto at room temperature, followed by stirring for 23 hrs. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, a saturated aqueous solution of ammonium chloride and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, to which ethyl acetate (2.5 ml) was added to precipitate crystals. The crystals were filtered off and dried under aeration to provide the titled compound (10.4 mg, 41%) as white crystals.

Workup

  1. customat room temperature
  2. concentrationThe reaction mixture was concentrated under a reduced pressure
  3. customto give a residue, which
  4. customat room temperature
  5. stirringby stirring for 23 hrs
  6. customThe reaction mixture was partitioned between ethyl acetate and water
  7. washThe organic layer was washed with water
  8. dry with materiala saturated aqueous solution of ammonium chloride and brine in this order, and dried over anhydrous sodium sulfate
  9. customThe solvent was evaporated
  10. customto give a residue
  11. customto precipitate crystals
  12. filtrationThe crystals were filtered off
  13. customdried under aeration

Sources & evidence

ORD record
ord-ae97e0515abc4cbbb02b4976e23d58df
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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