4-(4-Chloro-phenyl)-5-cyclopropylmethoxy-pyridine-2-carboxylic acid → 4-(4-chlorophenyl)-5-(cyclopropylmethoxy)-N-((3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)methyl)picolinamide

HRID 1528422Notes

Reaction equation

HRID 1528422 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([O:14][CH2:15][CH:16]3[CH2:18][CH2:17]3)=[CH:12][N:11]=[C:10]([C:19]([OH:21])=O)[CH:9]=2)=[CH:4][CH:3]=1.Cl.[F:23][C:24]([F:33])([F:32])[C:25]1[N:29]=[C:28]([CH2:30][NH2:31])[O:27][N:26]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]([O:14][CH2:15][CH:16]3[CH2:17][CH2:18]3)=[CH:12][N:11]=[C:10]([C:19]([NH:31][CH2:30][C:28]3[O:27][N:26]=[C:25]([C:24]([F:33])([F:32])[F:23])[N:29]=3)=[O:21])[CH:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 666786854-(4-Chloro-phenyl)-5-cyclopropylmethoxy-pyridine-2-carboxylic acidHCID 66687518[3-(Trifluoromethyl)-1,2,4-oxadiazol-5-yl]methanamine hydrochloride

Product 1

HCID 569283774-(4-chlorophenyl)-5-(cyclopropylmethoxy)-N-((3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)methyl)picolinamide

Procedure

The title compound was synthesized in analogy to Example 1, using 4-(4-chloro-phenyl)-5-(cyclopropylmethyloxy)-pyridine-2-carboxylic acid (example H) and C-(3-trifluoromethyl-[1,2,4]oxadiazol-5-yl)-methylamine hydrochloride (CAS registry No. 944905-93-5; example AK) as starting materials; LC-MS (UV peak area/ESI) 100%, 453.0924 (M+H)+.

Sources & evidence

ORD record
ord-feec263c6afc46b3852e088d69467ed1
Source dataset
uspto-grants-2015_07
Patent number
US09090599B2

Reaction notes

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