Triethylamine → HCID 69099654, compound

HRID 2251572Notes

Reaction equation

HRID 2251572 reaction equation
[NH2:1]/[C:2](/[N:5]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[N:31]=[C:32]([CH:35]3[CH2:37][CH2:36]3)[O:33][CH:34]=2)=[CH:26][CH:25]=1)[CH2:6][CH2:7][C:8]1[CH:22]=[CH:21][C:11]([O:12][C:13]([CH3:20])([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=1)=[N:3]\[OH:4].C(N(CC)CC)C.[F:45][C:46]([F:57])([F:56])[C:47]1[CH:48]=[C:49]([CH:53]=[CH:54][CH:55]=1)[C:50](Cl)=O>C1(C)C=CC=CC=1>[CH:35]1([C:32]2[O:33][CH:34]=[C:30]([C:27]3[CH:26]=[CH:25][C:24]([CH2:23][N:5]([C:2]4[N:1]=[C:50]([C:49]5[CH:53]=[CH:54][CH:55]=[C:47]([C:46]([F:45])([F:56])[F:57])[CH:48]=5)[O:4][N:3]=4)[CH2:6][CH2:7][C:8]4[CH:22]=[CH:21][C:11]([O:12][C:13]([CH3:20])([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=4)=[CH:29][CH:28]=3)[N:31]=2)[CH2:36][CH2:37]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 87693991HCID 87693991, compound

Product 1

HCID 69099654HCID 69099654, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a cooled solution of ethyl 2-[4-(2-{[(E)-amino(hydroxyimino)methyl][4-(2-cyclopropyl-1,3-oxazol-4-yl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (0.108 g, 0.21 mmol) in toluene (2 ml) was added triethylamine (0.028 mL, 0.20 mmol) dropwise. After 5 min, 3-(trifluoromethyl)benzoyl chloride (0.031 ml, 0.20 mmol) in toluene (0.1 ml) was added dropwise. The mixture was allowed to warm to rt over 2 h and then heated to 110C for 2 hr. Upon cooling, the mixture was filtered, and the solid was washed with EtOAc. The filtrate was concentrated in vacuo, and the resulting residue was partitioned between EtOAc and a solution of 0.5N aqueous HCl. The organic phase was washed with 0.5N aqueous HCl (1×), 0.5N aqueous NaOH (2×), and brine (1×), dried with Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (EtOAc/hexanes, 10:90 to 20:80) to yield ethyl 2-{4-[2-([4-(2-cyclopropyl-1,3-oxazol-4-yl)benzyl]{5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}amino)ethyl]phenoxy}-2-methylpropanoate (76 mg, 58%).

Workup

  1. temperatureUpon cooling
  2. filtrationthe mixture was filtered
  3. washthe solid was washed with EtOAc
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe resulting residue was partitioned between EtOAc
  6. washThe organic phase was washed with 0.5N aqueous HCl (1×), 0.5N aqueous NaOH (2×), and brine (1×)
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by flash chromatography (EtOAc/hexanes, 10:90 to 20:80)

Sources & evidence

ORD record
ord-e0611427e79d401fb344b067c3c9c079
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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