5-Bromopyridine-2-carboxylic acid → 5-Bromo-N-[1-(cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidin-3-yl]pyridine-2-carboxamide

HRID 876291

Reaction equation

HRID 876291 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([C:13]([N:15]2[CH2:20][CH:19]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH3:28])=[CH:23][CH:22]=3)[CH2:18][CH:17]([NH2:29])[CH2:16]2)=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]1.[Br:30][C:31]1[CH:32]=[CH:33][C:34]([C:37](O)=[O:38])=[N:35][CH:36]=1>>[Br:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]([NH:29][CH:17]2[CH2:18][CH:19]([C:21]3[CH:22]=[CH:23][C:24]([CH2:27][CH3:28])=[CH:25][CH:26]=3)[CH2:20][N:15]([C:13]([CH:8]3[CH2:9][CH2:10][CH2:11][CH2:12]3)=[O:14])[CH2:16]2)=[O:38])=[N:35][CH:36]=1

Participants

3

Reactant 2

HCID 6085445-Bromopyridine-2-carboxylic acidHCID 667013441-(Cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidine-3-amine trifluoroacetate

Product 1

HCID 667615095-Bromo-N-[1-(cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidin-3-yl]pyridine-2-carboxamide

Procedure

139 mg (0.34 mmol) of 1-(cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidine-3-amine trifluoroacetate (Example 8A) and 68 mg (0.34 mmol, 1.0 eq.) of 5-bromopyridine-2-carboxylic acid were reacted according to General Method 1. Yield: 75 mg (44% of theory)

Sources & evidence

ORD record
ord-18accb3768bb478392ef44bd3b7fec4b
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Linked notes

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