Potassium Carbonate → {3-(3-Ethoxy-1,2,4-oxadiazol-5-yl)-5-[3-fluoro-4-(trifluoromethoxy)phenyl]piperidin-1-yl}(3-hydroxyazetidin-1-yl)methanone

HRID 661316Notes

Reaction equation

HRID 661316 reaction equation
[CH2:1]([O:3][C:4]1[N:8]=[C:7]([CH:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[C:17]([F:26])[CH:16]=3)[CH2:12][N:11]([C:27]([O:29]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:10]2)[O:6][N:5]=1)[CH3:2].Cl.[OH:40][CH:41]1[CH2:44][NH:43][CH2:42]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4]1[N:8]=[C:7]([CH:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:23])([F:25])[F:24])=[C:17]([F:26])[CH:16]=3)[CH2:12][N:11]([C:27]([N:43]3[CH2:44][CH:41]([OH:40])[CH2:42]3)=[O:29])[CH2:10]2)[O:6][N:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27592903-Hydroxyazetidine hydrochlorideHCID 581165474-Nitrophenyl 3-(3-ethoxy-1,2,4-oxadiazol-5-yl)-5-[3-fluoro-4-(trifluoromethoxy)phenyl]-piperidine-1-carboxylate

Product 1

HCID 58116512{3-(3-Ethoxy-1,2,4-oxadiazol-5-yl)-5-[3-fluoro-4-(trifluoromethoxy)phenyl]piperidin-1-yl}(3-hydroxyazetidin-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

145 mg (0.23 mmol) of the compound from Example 65A, 76 mg (0.68 mmol) of 3-hydroxyazetidine hydrochloride and 62 mg (0.45 mmol) of potassium carbonate were initially charged in 4.5 ml of DMF and reacted in the microwave at 150° C. for 15 minutes. The reaction mixture was purified by means of preparative HPLC. Yield: 41 mg (36% of theory)

Workup

  1. customreacted in the microwave at 150° C. for 15 minutes
  2. customThe reaction mixture was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-2d0367b15449401ca8c7d6e00a455481
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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