Hydrochloric Acid → N-[5-(5-Ethyl-[1,2,4]oxadiazol-3-yl)-4-phenyl-thiazol-2-yl]-propionamide

HRID 604486Notes

Reaction equation

HRID 604486 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:13]([NH:15][OH:16])=[NH:14])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.C(N(C(C)C)[CH:20]([CH3:22])[CH3:21])C.[C:26](Cl)(=[O:29])[CH2:27][CH3:28].Cl>C1COCC1.C(O)C>[CH2:20]([C:22]1[O:16][N:15]=[C:13]([C:4]2[S:3][C:2]([NH:1][C:26](=[O:29])[CH2:27][CH3:28])=[N:6][C:5]=2[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:14]=1)[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 178513412HCID 178513412, compound

Product 1

HCID 57709613N-[5-(5-Ethyl-[1,2,4]oxadiazol-3-yl)-4-phenyl-thiazol-2-yl]-propionamideYield 49%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-N-hydroxy-4-phenyl-thiazole-5-carboxamidine (1.5 g, 6.4 mmol) was dissolved in dry THF (50 mL). Ethyl-diisopropyl-amine (2.5 mL) and propionylchloride (2.8 mL, 5 eq) was added. The reaction mixture was stirred overnight at room temperature. pH was adjusted to pH ˜2 by addition of HCl in ethanol. The reaction mixture was stirred overnight at room temperature. The solvent was evaporated to yield a yellow oil. The crude product was purified by flash column chromatography, eluted with 30% ethyl acetate in hexanes to give the product as a white solid. Yield: 49%.

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. customThe solvent was evaporated
  3. customto yield a yellow oil
  4. customThe crude product was purified by flash column chromatography
  5. washeluted with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c57bc49a4900416d8d700da8cf4fb648
Source dataset
uspto-grants-2011_03
Patent number
US07910613B2

Reaction notes

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