Dimethylformamide → HCID 23153513, compound

HRID 492828Notes

Reaction equation

HRID 492828 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:28])[CH2:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[O:19])=[C:11]([CH3:29])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:30][N:31]([CH3:34])[CH:32]=[O:33].C(N(CC)CC)C.ClC(OC1C=CC=CC=1)=O>O1CCCC1.C(O)C.C(OCC)C>[CH3:30][N:31]([CH3:34])[C:32](=[O:33])[NH:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:28])[CH2:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[O:19])=[C:11]([CH3:29])[CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 23153052HCID 23153052, compound

Product 1

HCID 23153513HCID 23153513, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[4-(2-aminopyridin-4-yloxy)-2-methylphenyl]-N′-(4-fluorophenyl)malonamide (60 mg) in tetrahydrofuran (6 ml)-N,N-dimethylformamide (0.090 ml) was added triethylamine (0.042 ml), and then phenyl chloroformate (0.038 ml) was added thereto while cooling in an ice water bath, followed by stirring for 20 min. The reaction mixture was concentrated under a reduced pressure. To a suspension of the residue in N,N-dimethylformamide (2.4 ml) were added diethylamine hydrochloride (61 mg) and triethylamine (0.106 ml), followed by stirring at room temperature for 7 hrs and 20 min. The reaction mixture was partitioned between ethyl acetate (50 ml) and a 1 N aqueous solution of sodium hydroxide (30 ml). The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then suspended in ethanol (0.5 ml)-diethyl ether (5 ml), filtered off, washed with diethyl ether and dried under aeration to provide the titled compound (52.7 mg, 75%) as colorless powder.

Workup

  1. temperaturewhile cooling in an ice water bath
  2. concentrationThe reaction mixture was concentrated under a reduced pressure
  3. additionTo a suspension of the residue in N,N-dimethylformamide (2.4 ml)
  4. additionwere added diethylamine hydrochloride (61 mg) and triethylamine (0.106 ml)
  5. stirringby stirring at room temperature for 7 hrs and 20 min
  6. customThe reaction mixture was partitioned between ethyl acetate (50 ml)
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated
  10. customto give a residue, which
  11. filtrationfiltered off
  12. washwashed with diethyl ether
  13. customdried under aeration

Sources & evidence

ORD record
ord-1c3b544114224a71a61c9a0781f42293
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

Loading…