N'-Hydroxycyclopropanecarboximidamide → 1-({3-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}-carbonyl)piperidine-4-carbonitrile

HRID 1643161Notes

Reaction equation

HRID 1643161 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]([CH:35]1[CH2:37][CH2:36]1)[NH2:34]>>[CH:35]1([C:33]2[N:34]=[C:28]([CH:13]3[CH2:14][CH:15]([C:17]4[CH:22]=[CH:21][C:20]([O:23][C:24]([F:25])([F:27])[F:26])=[CH:19][CH:18]=4)[CH2:16][N:11]([C:9]([N:6]4[CH2:7][CH2:8][CH:3]([C:1]#[N:2])[CH2:4][CH2:5]4)=[O:10])[CH2:12]3)[O:30][N:32]=2)[CH2:37][CH2:36]1

Participants

3

Reactant 2

HCID 2794666N'-HydroxycyclopropanecarboximidamideHCID 580027061-[(4-Cyanopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acid

Product 1

HCID 580023521-({3-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethoxy)phenyl]piperidin-1-yl}-carbonyl)piperidine-4-carbonitrile

Procedure

100 mg (about 0.153 mmol) of the compound from Example 108A and 30 mg (0.306 mmol) of N′-hydroxycyclopropanecarboximidamide were reacted according to the General Method 2. Yield: 312 mg (41% of theory)

Sources & evidence

ORD record
ord-42bd2f3eb49e4b3fb8515131888daf54
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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