5-Chloronicotinic acid → 5-Chloro-N-[1-(cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidin-3-yl]pyridine-3-carboxamide

HRID 876290

Reaction equation

HRID 876290 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.[Cl:30][C:31]1[CH:32]=[C:33]([C:37](O)=[O:38])[CH:34]=[N:35][CH:36]=1>>[Cl:30][C:31]1[CH:32]=[C:33]([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])[CH:34]=[N:35][CH:36]=1

Participants

3

Reactant 2

HCID 2479865-Chloronicotinic acidHCID 667013441-(Cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidine-3-amine trifluoroacetate

Product 1

HCID 469317455-Chloro-N-[1-(cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidin-3-yl]pyridine-3-carboxamide

Procedure

65 mg (0.15 mmol) of 1-(cyclopentylcarbonyl)-5-(4-ethylphenyl)piperidine-3-amine trifluoroacetate (Example 8A) and 21 mg (0.13 mmol, 0.9 eq.) of 5-chloropyridine-3-carboxylic acid were reacted according to General Method 1. Yield: 39 mg (62% of theory)

Sources & evidence

ORD record
ord-dbf24134a32a45f1ac814cab6ee02d4e
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Linked notes

Loading…