2-fluoro-N'-hydroxybenzene-1-carboximidamide → {3-[3-(2-Fluorophenyl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}(4-hydroxypiperidin-1-yl)methanone

HRID 1642947Notes

Reaction equation

HRID 1642947 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]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[CH2:13][CH:12]([C:27](O)=O)[CH2:11]2)=[O:9])[CH2:4][CH2:3]1.[F:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37](=[N:39][OH:40])[NH2:38]>>[F:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]1[N:38]=[C:27]([CH:12]2[CH2:13][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:24])([F:26])[F:25])=[CH:18][CH:17]=3)[CH2:15][N:10]([C:8]([N:5]3[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]3)=[O:9])[CH2:11]2)[O:40][N:39]=1

Participants

3

Reactant 2

HCID 32595892-fluoro-N'-hydroxybenzene-1-carboximidamideHCID 580024151-[(4-Hydroxypiperidin-1-yl)carbonyl]-5-[4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acid

Product 1

HCID 58002324{3-[3-(2-Fluorophenyl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}(4-hydroxypiperidin-1-yl)methanone

Procedure

100 mg (0.24 mmol) of 1-[(4-hydroxypiperidin-1-yl)carbonyl]-5-[4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acid (Example 63A) and 56 mg (0.36 mmol, 1.5 eq.) of 2-fluoro-N′-hydroxybenzenecarboximidamide were reacted according to the General Method 2. Yield: 73 mg (57% of theory)

Sources & evidence

ORD record
ord-6a95652ca1914283a540f7d1bffa110d
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

Loading…