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

HRID 1643010Notes

Reaction equation

HRID 1643010 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].[CH:30]1([N:33]2[CH2:38][CH2:37][CH:36]([C:39](=[N:41]O)[NH2:40])[CH2:35][CH2:34]2)[CH2:32][CH2:31]1>>[CH:30]1([N:33]2[CH2:38][CH2:37][CH:36]([C:39]3[N:41]=[C:27]([CH:13]4[CH2:14][CH:15]([C:17]5[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=5)[CH2:16][N:11]([C:9]([N:6]5[CH2:7][CH2:8][CH:3]([C:1]#[N:2])[CH2:4][CH2:5]5)=[O:10])[CH2:12]4)[O:28][N:40]=3)[CH2:35][CH2:34]2)[CH2:31][CH2:32]1

Participants

3

Reactant 2

HCID 580023321-[(4-Cyanopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acidHCID 723495471-cyclopropyl-N-hydroxypiperidine-4-carboxamidine

Product 1

HCID 580024541-({3-[3-(1-Cyclopropylpiperidin-4-yl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethyl)phenyl]-piperidin-1-yl}carbonyl)piperidine-4-carbonitrile

Procedure

155 mg (0.363 mmol) of the compound from Example 100A and 100 mg (0.545 mmol) of the compound from Example 75A were reacted according to the General Method 2. Yield: 76 mg (38% of theory)

Sources & evidence

ORD record
ord-c2510fbb9a594f95b8642085ff2aae7a
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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