1-[(4-Hydroxypiperidin-1-yl)carbonyl]-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylic acid → (4-Hydroxypiperidin-1-yl) {3-(3-isopropoxy-1,2,4-oxadiazol-5-yl)-5-[4-(2,2,2-trifluoroethyl)-phenyl]piperidin-1-yl}methanone

HRID 661308Notes

Reaction equation

HRID 661308 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([N:10]2[CH2:15][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[CH2:13][CH:12]([C:27]([OH:29])=O)[CH2:11]2)=[O:9])[CH2:4][CH2:3]1.O[N:31]=[C:32]([O:34][CH:35]([CH3:37])[CH3:36])[NH2:33]>>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([N:10]2[CH2:15][CH:14]([C:16]3[CH:17]=[CH:18][C:19]([CH2:22][C:23]([F:25])([F:24])[F:26])=[CH:20][CH:21]=3)[CH2:13][CH:12]([C:27]3[O:29][N:33]=[C:32]([O:34][CH:35]([CH3:37])[CH3:36])[N:31]=3)[CH2:11]2)=[O:9])[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 581165041-[(4-Hydroxypiperidin-1-yl)carbonyl]-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylic acidHCID 76225143isopropyl N-hydroxyimidocarbamate

Product 1

HCID 58116553(4-Hydroxypiperidin-1-yl) {3-(3-isopropoxy-1,2,4-oxadiazol-5-yl)-5-[4-(2,2,2-trifluoroethyl)-phenyl]piperidin-1-yl}methanone

Procedure

According to General Method 1, 150 mg (0.362 mmol) of the compound from Example 58A and 62.7 mg (0.398 mmol, purity 75%) of isopropyl N′-hydroxyimidocarbamate [G. Zinner, G. Nebel, Arch. Pharm. 1970, 303, 385-390] were reacted. Yield: 41.6 mg (23% of theory).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-fa20f59acb514f7a926a4f89e12edbe3
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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