1-[(4-Cyanopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acid → 1-({3-[3-(2-Hydroxy-2-methylpropyl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethyl)phenyl]-piperidin-1-yl}carbonyl)piperidine-4-carbonitrile

HRID 1643002Notes

Reaction equation

HRID 1643002 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([N:11]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[CH2:14][CH:13]([C:27](O)=[O:28])[CH2:12]2)=[O:10])[CH2:5][CH2:4]1)#[N:2].O[N:31]=[C:32]([NH2:38])[CH2:33][C:34]([OH:37])([CH3:36])[CH3:35]>>[OH:37][C:34]([CH3:36])([CH3:35])[CH2:33][C:32]1[N:38]=[C:27]([CH:13]2[CH2:14][CH:15]([C:17]3[CH:18]=[CH:19][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:21][CH:22]=3)[CH2:16][N:11]([C:9]([N:6]3[CH2:7][CH2:8][CH:3]([C:1]#[N:2])[CH2:4][CH2:5]3)=[O:10])[CH2:12]2)[O:28][N:31]=1

Participants

3

Reactant 2

HCID 580023321-[(4-Cyanopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acidHCID 86636894N',3-dihydroxy-3-methylbutanimidamide

Product 1

HCID 580026881-({3-[3-(2-Hydroxy-2-methylpropyl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethyl)phenyl]-piperidin-1-yl}carbonyl)piperidine-4-carbonitrile

Procedure

80 mg (0.188 mmol) of the compound from Example 100A and 52 mg (0.281 mmol) of N′,3-dihydroxy-3-methylbutanimidamide were reacted according to the General Method 2. Yield: 65 mg (67% of theory)

Sources & evidence

ORD record
ord-75878ac3ba6c42798b07ec8b04aba6b8
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

Loading…