2-Methoxypyrimidine-5-boronic acid → [6-(2-Methoxy-pyrimidin-5-yl)-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 1517108Notes

Reaction equation

HRID 1517108 reaction equation
COC(=O)C1C(C)=CC(C2C=CC=C(C(F)(F)F)C=2)=NC=1OC.Cl[C:25]1[N:30]=[C:29]([C:31]([N:33]2[CH2:38][CH2:37][CH:36]([N:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)[CH2:35][CH2:34]2)=[O:32])[C:28]([CH3:44])=[CH:27][C:26]=1[C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:54])([F:53])[F:52])[CH:46]=1.[CH3:55][O:56][C:57]1[N:62]=[CH:61][C:60](B(O)O)=[CH:59][N:58]=1>>[CH3:55][O:56][C:57]1[N:62]=[CH:61][C:60]([C:25]2[N:30]=[C:29]([C:31]([N:33]3[CH2:38][CH2:37][CH:36]([N:39]4[CH2:43][CH2:42][CH2:41][CH2:40]4)[CH2:35][CH2:34]3)=[O:32])[C:28]([CH3:44])=[CH:27][C:26]=2[C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:54])([F:53])[F:52])[CH:46]=2)=[CH:59][N:58]=1

Participants

4

Reactant 3

HCID 27367782-Methoxypyrimidine-5-boronic acidHCID 44547211[6-Chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanoneHCID 57441128HCID 57441128, compound

Product 1

HCID 58016710[6-(2-Methoxy-pyrimidin-5-yl)-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Procedure

In analogy to the procedure described for the preparation of intermediate 5C, [6-chloro-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 3) was reacted with 2-methoxypyrimidin-5-yl-boronic acid to give the title compound as light brown amorphous solid. MS: 526.2 (MH+).

Sources & evidence

ORD record
ord-5b6a7388ff3346189524c115315c5426
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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