5-[3-Fluoro-4-(trifluoromethyl)phenyl]-1-(thiomorpholin-4-ylcarbonyl)piperidine-3-carboxylic acid → {3-(3-Ethoxy-1,2,4-oxadiazol-5-yl)-5-[3-fluoro-4-(trifluoromethyl)phenyl]piperidin-1-yl}(thiomorpholin-4-yl)methanone

HRID 661314Notes

Reaction equation

HRID 661314 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]2[CH2:17][N:16]([C:18]([N:20]3[CH2:25][CH2:24][S:23][CH2:22][CH2:21]3)=[O:19])[CH2:15][CH:14]([C:26]([OH:28])=O)[CH2:13]2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].O[N:30]=[C:31]([O:33][CH2:34][CH3:35])[NH2:32]>>[CH2:34]([O:33][C:31]1[N:32]=[C:26]([CH:14]2[CH2:13][CH:12]([C:4]3[CH:5]=[CH:6][C:7]([C:8]([F:9])([F:11])[F:10])=[C:2]([F:1])[CH:3]=3)[CH2:17][N:16]([C:18]([N:20]3[CH2:21][CH2:22][S:23][CH2:24][CH2:25]3)=[O:19])[CH2:15]2)[O:28][N:30]=1)[CH3:35]

Participants

3

Reactant 2

HCID 581164635-[3-Fluoro-4-(trifluoromethyl)phenyl]-1-(thiomorpholin-4-ylcarbonyl)piperidine-3-carboxylic acidHCID 76223295ethyl N-hydroxyimidocarbamate

Product 1

HCID 58116531{3-(3-Ethoxy-1,2,4-oxadiazol-5-yl)-5-[3-fluoro-4-(trifluoromethyl)phenyl]piperidin-1-yl}(thiomorpholin-4-yl)methanone

Procedure

According to General Method 4, 151 mg (0.280 mmol) of the compound from Example 85A and 43 mg (0.420 mmol) of ethyl N′-hydroxyimidocarbamate [G. Zinner, G. Nebel, Arch. Pharm. 1970, 303, 385-390] were reacted. Yield: 38 mg (25% of theory).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-448dd86778494d4aac87ca5d6aa2f702
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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