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

HRID 1642987Notes

Reaction equation

HRID 1642987 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]([NH2:39])[CH2:33][C:34]1([CH2:37][OH:38])[CH2:36][CH2:35]1>>[OH:38][CH2:37][C:34]1([CH2:33][C:32]2[N:39]=[C:27]([CH:13]3[CH2:14][CH:15]([C:17]4[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][CH:18]=4)[CH2:16][N:11]([C:9]([N:6]4[CH2:5][CH2:4][CH:3]([C:1]#[N:2])[CH2:8][CH2:7]4)=[O:10])[CH2:12]3)[O:28][N:31]=2)[CH2:36][CH2:35]1

Participants

3

Reactant 2

HCID 580023321-[(4-Cyanopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylic acidHCID 79009133N'-Hydroxy-2-[1-(hydroxymethyl)cyclopropyl]ethanimidamide

Product 1

HCID 580024401-({3-(3-{[1-(Hydroxymethyl)cyclopropyl]methyl}-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)-phenyl]piperidin-1-yl}carbonyl)piperidine-4-carbonitrile

Procedure

100 mg (0.24 mmol) of the compound from Example 100A and 61 mg (0.37 mmol) of the compound from Example 67A were reacted according to the General Method 2. Yield: 70 mg (56% of theory)

Sources & evidence

ORD record
ord-da82d13f5a53404e92dff825627f7aa2
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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