Water → 2-(1,4-Bis-(4-fluoro-phenyl)-1H-imidazol-2-yl)-1-(2-methyl-6,7-dihydro-4H-oxazolo[5,4-c]pyridin-5-yl)-ethanone

HRID 1019640Notes

Reaction equation

HRID 1019640 reaction equation
C(O[C:4](=[O:25])[CH2:5][C:6]1[N:7]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:10]=1)C.Cl.[CH3:27][C:28]1[O:29][C:30]2[CH2:31][NH:32][CH2:33][CH2:34][C:35]=2[N:36]=1.CCN(C(C)C)C(C)C.O>CN1C(=O)CCC1>[F:24][C:21]1[CH:20]=[CH:19][C:18]([N:7]2[CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[N:10]=[C:6]2[CH2:5][C:4]([N:32]2[CH2:33][CH2:34][C:35]3[N:36]=[C:28]([CH3:27])[O:29][C:30]=3[CH2:31]2)=[O:25])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 86687938(1,4-bis-(4-fluoro-phenyl)-1H-imidazol-2-yl)-acetic acid ethyl esterHCID 866879402-Methyl-4,5,6,7-tetrahydrooxazolo[5,4-c]pyridine;hydrochloride

Product 1

HCID 716042642-(1,4-Bis-(4-fluoro-phenyl)-1H-imidazol-2-yl)-1-(2-methyl-6,7-dihydro-4H-oxazolo[5,4-c]pyridin-5-yl)-ethanoneYield 19.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

70 mg (1,4-bis-(4-fluoro-phenyl)-1H-imidazol-2-yl)-acetic acid ethyl ester, 55 mg 2-methyl-4,5,6,7-tetrahydro-oxazolo[5,4-c]pyridine hydrochloride and 0.1 mL DIPEA in 2 mL NMP was stirred 50 min at 180° C. under microwave condition. The reaction was poured into water and extracted with EtOAC. The organic layer was dried with magnesium sulfate and evaporated the residue was purified by HPLC (Waters Symmetry 50×140 mm water+0,3% HCOOH/methanoll 10% until 90% in 14 min) to yield 17 mg desired product. Rt: 1.10 (method A), (M+H)+: 435

Workup

  1. extractionextracted with EtOAC
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. customevaporated the residue
  4. customwas purified by HPLC (Waters Symmetry 50×140 mm water+0,3% HCOOH/methanoll 10% until 90% in 14 min)

Sources & evidence

ORD record
ord-2121e5c0a1d44fe89f5505877636c703
Source dataset
uspto-grants-2014_05
Patent number
US08716277B2

Reaction notes

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