2-Bromo-5-chloro-3-fluoropyridine → ((2S,3R)-2-(((5-Chloro-3-fluoropyridin-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(5-methyl-2-(pyrimidin-2-yl)phenyl)methanone

HRID 61109Notes

Reaction equation

HRID 61109 reaction equation
[NH2:1][CH2:2][C@@H:3]1[C@H:8]([CH3:9])[CH2:7][CH2:6][CH2:5][N:4]1[C:10]([C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[C:19]1[N:24]=[CH:23][CH:22]=[CH:21][N:20]=1)=[O:11].Br[C:26]1[C:31]([F:32])=[CH:30][C:29]([Cl:33])=[CH:28][N:27]=1>>[Cl:33][C:29]1[CH:30]=[C:31]([F:32])[C:26]([NH:1][CH2:2][C@@H:3]2[C@H:8]([CH3:9])[CH2:7][CH2:6][CH2:5][N:4]2[C:10]([C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=2[C:19]2[N:20]=[CH:21][CH:22]=[CH:23][N:24]=2)=[O:11])=[N:27][CH:28]=1

Participants

3

Reactant 2

HCID 109657982-Bromo-5-chloro-3-fluoropyridineHCID 117727676((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(pyrimidin-2-yl)phenyl)methanone

Product 1

HCID 117727778((2S,3R)-2-(((5-Chloro-3-fluoropyridin-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(5-methyl-2-(pyrimidin-2-yl)phenyl)methanone

Procedure

The title compound was prepared following the same general protocol as described for Example A44 using ((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(pyrimidin-2-yl)phenyl)methanone and 2-bromo-5-chloro-3-fluoropyridine. MS (ESI) 454 (M+H).

Sources & evidence

ORD record
ord-6602e8a174f746cd9e833297b9a14c07
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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