2-Iodo-3-methylbenzoic acid → ((2S,3R)-3-Methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)(3-methyl-2-(pyrimidin-2-yl)phenyl)methanone

HRID 61241Notes

Reaction equation

HRID 61241 reaction equation
IC1C(C)=CC=CC=1C(O)=O.[NH2:12][CH2:13][C@@H:14]1[C@H:19]([CH3:20])[CH2:18][CH2:17][CH2:16][N:15]1[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:24]=1[C:30]1[N:35]=[CH:34][CH:33]=[CH:32][N:31]=1)=[O:22].F[C:37]1[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][N:38]=1>>[CH3:20][C@@H:19]1[CH2:18][CH2:17][CH2:16][N:15]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:24]=2[C:30]2[N:31]=[CH:32][CH:33]=[CH:34][N:35]=2)=[O:22])[C@@H:14]1[CH2:13][NH:12][C:37]1[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][N:38]=1

Participants

4

Reactant 3

HCID 27593652-Iodo-3-methylbenzoic acidHCID 54637542-Fluoro-5-(trifluoromethyl)pyridineHCID 117727882((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(3-methyl-2-(pyrimidin-2-yl)phenyl)methanone

Product 1

HCID 117728000((2S,3R)-3-Methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidin-1-yl)(3-methyl-2-(pyrimidin-2-yl)phenyl)methanone

Procedure

The title compound was prepared following the same general protocol as described for Example A230 using 2-iodo-3-methylbenzoic acid to make ((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(3-methyl-2-(pyrimidin-2-yl)phenyl)methanone and 2-fluoro-5-(trifluoromethyl)pyridine. ESI-MS (m/z): 470 [M+1]+.

Sources & evidence

ORD record
ord-efa79bbc0a804747a258041be08104d3
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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