Dimethylamine → HCID 10209934, compound

HRID 1610959Notes

Reaction equation

HRID 1610959 reaction equation
[CH3:1][NH:2][CH3:3].[F:4][C:5]([F:42])([F:41])[C:6]1[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]2[O:15][CH:16]=[C:17]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][N:31]4[CH:35]=[CH:34][N:33]=[C:32]4[CH2:36][CH2:37][C:38](O)=[O:39])=[CH:23][CH:22]=3)[N:18]=2)=[CH:8][CH:7]=1.C(N(CC)CC)C.O>C1COCC1.P(C#N)(OCC)(OCC)=O.CN(C=O)C>[CH3:1][N:2]([CH3:3])[C:38](=[O:39])[CH2:37][CH2:36][C:32]1[N:31]([CH2:30][CH2:29][CH2:28][CH2:27][C:24]2[CH:23]=[CH:22][C:21]([O:20][CH2:19][C:17]3[N:18]=[C:14](/[CH:13]=[CH:12]/[C:9]4[CH:8]=[CH:7][C:6]([C:5]([F:41])([F:4])[F:42])=[CH:11][CH:10]=4)[O:15][CH:16]=3)=[CH:26][CH:25]=2)[CH:35]=[CH:34][N:33]=1

Participants

8

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 8471TriethylamineHCID 22259309HCID 22259309, compound

Product 1

HCID 10209934HCID 10209934, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 76257Diethyl cyanophosphonateSolvent

Procedure

A solution (2M; 0.557 ml) of N,N-dimethylamine in THF and diethyl cyanophosphate (67.6 μl) were added to a solution of 3-[1-[4-[4-[[2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-imidazol-2-yl]propionic acid (200 mg) in DMF (3 ml) at 0° C., and the mixture was stirred for 15 min. Triethylamine (77.6 μl) was added to the mixture at 0° C., and the mixture was stirred at room temperature for 16 hr. The reaction mixture was combined with water and extracted with ethyl acetate. The extract was successively washed with water and saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; dichloromethane to dichloromethane:methanol=20:1) and recrystallized from diethyl ether-ethyl acetate-hexane to give the titled compound (146 mg) as a colorless crystal powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hr
  2. extractionextracted with ethyl acetate
  3. washThe extract was successively washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent; dichloromethane to dichloromethane:methanol=20:1)
  7. customrecrystallized from diethyl ether-ethyl acetate-hexane

Sources & evidence

ORD record
ord-da733f27b966469bbf86e6174853b303
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

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