1-[(3-Hydroxyazetidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid → (3-Hydroxyazetidin-1-yl) {3-{3-[2-(propan-2-yloxy)ethyl]-1,2,4-oxadiazol-5-yl}-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}methanone

HRID 1642992Notes

Reaction equation

HRID 1642992 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([N:8]2[CH2:13][CH:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[CH2:11][CH:10]([C:24]([OH:26])=O)[CH2:9]2)=[O:7])[CH2:3]1.O[N:28]=[C:29]([NH2:36])[CH2:30][CH2:31][O:32][CH:33]([CH3:35])[CH3:34]>>[OH:1][CH:2]1[CH2:3][N:4]([C:6]([N:8]2[CH2:13][CH:12]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=3)[CH2:11][CH:10]([C:24]3[O:26][N:36]=[C:29]([CH2:30][CH2:31][O:32][CH:33]([CH3:35])[CH3:34])[N:28]=3)[CH2:9]2)=[O:7])[CH2:5]1

Participants

3

Reactant 2

HCID 580025781-[(3-Hydroxyazetidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acidHCID 74045961N-Hydroxy-3-(1-methylethoxy)-propanimidamide

Product 1

HCID 58002553(3-Hydroxyazetidin-1-yl) {3-{3-[2-(propan-2-yloxy)ethyl]-1,2,4-oxadiazol-5-yl}-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}methanone

Procedure

100 mg (0.27 mmol) of the compound from Example 101A and 66 mg (0.40 mmol) of the compound from Example 65A were reacted according to the General Method 2. Yield: 28 mg (20% of theory)

Sources & evidence

ORD record
ord-5a8748e640d24aebb3a2f52454845b09
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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