2-Chloro-5-(trifluoromethyl)pyrimidine → (2,3-Difluoro-6-(2H-1,2,3-triazol-2-yl)phenyl)((2S,3R)-3-methyl-2-(((5-(trifluoromethyl)pyrimidin-2-yl)amino)methyl)piperidin-1-yl)methanone

HRID 61261Notes

Reaction equation

HRID 61261 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]([N:12]2[N:16]=[CH:15][CH:14]=[N:13]2)[C:3]=1[C:4]([OH:6])=O.[CH3:17][C@@H:18]1[CH2:23][CH2:22][CH2:21][NH:20][C@@H:19]1[CH2:24][N:25]1[C:33](=O)C2C(=CC=CC=2)C1=O.ClC1[N:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][N:38]=1>>[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]([N:12]2[N:16]=[CH:15][CH:14]=[N:13]2)[C:3]=1[C:4]([N:20]1[CH2:21][CH2:22][CH2:23][C@@H:18]([CH3:17])[C@H:19]1[CH2:24][NH:25][C:33]1[N:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][N:38]=1)=[O:6]

Participants

4

Reactant 3

HCID 133170192-Chloro-5-(trifluoromethyl)pyrimidineHCID 1177276302-(((2S,3R)-3-Methylpiperidin-2-yl)methyl)isoindoline-1,3-dioneHCID 1177278842,3-difluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid

Product 1

HCID 117728214(2,3-Difluoro-6-(2H-1,2,3-triazol-2-yl)phenyl)((2S,3R)-3-methyl-2-(((5-(trifluoromethyl)pyrimidin-2-yl)amino)methyl)piperidin-1-yl)methanone

Procedure

The title compound was prepared following the same general protocol as described in Example A1, using 2,3-difluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid, 2-(((2S,3R)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione and 2-chloro-5-(trifluoromethyl)pyrimidine. ESI-MS (m/z): 482 [M+1]+. 1H NMR (300 MHz, DMSO-d6) δ 8.75-7.05 (m, 7H), 5.05-2.70 (m, 5H), 1.95-0.65 (m, 8H).

Sources & evidence

ORD record
ord-29f9fb4f31b844a19817aa13afccffce
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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