n-Hydroxypivalimidamide → 1-({3-(3-tert-Butyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}carbonyl)-piperidine-4-carbonitrile

HRID 1642996Notes

Reaction equation

HRID 1642996 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]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:14][CH:13]([C:28]([OH:30])=O)[CH2:12]2)=[O:10])[CH2:5][CH2:4]1)#[N:2].O[N:32]=[C:33]([NH2:38])[C:34]([CH3:37])([CH3:36])[CH3:35]>>[C:34]([C:33]1[N:38]=[C:28]([CH:13]2[CH2:14][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:25])([F:27])[F:26])=[CH:19][CH:18]=3)[CH2:16][N:11]([C:9]([N:6]3[CH2:5][CH2:4][CH:3]([C:1]#[N:2])[CH2:8][CH2:7]3)=[O:10])[CH2:12]2)[O:30][N:32]=1)([CH3:37])([CH3:36])[CH3:35]

Participants

3

Reactant 2

HCID 2794841n-HydroxypivalimidamideHCID 580027061-[(4-Cyanopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acid

Product 1

HCID 580021951-({3-(3-tert-Butyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}carbonyl)-piperidine-4-carbonitrile

Procedure

85 mg (0.20 mmol) of 1-[(4-cyanopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethoxy)phenyl]-piperidine-3-carboxylic acid (Example 108A) and 35 mg (0.3 mmol) of N′-hydroxy-2,2-dimethylpropanimidamide were reacted according to the General Method 2. Yield: 61 mg (60% of theory).

Sources & evidence

ORD record
ord-838b6b6532f94893b8b1707f6e827f8b
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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