3,5-Dimethylisoxazole-4-boronic acid → (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5-(3,5-dimethylisoxazol-4-yl)-2-(methylthio)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

HRID 531317Notes

Reaction equation

HRID 531317 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25](Br)=[CH:24][N:23]=[C:22]([S:27][CH3:28])[N:21]=3)[C@H:14]2[CH3:29])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:32][C:33]1[C:37](B(O)O)=[C:36]([CH3:41])[O:35][N:34]=1.FC(F)(F)C1C=C([C@H]2OC(=O)N(CC3C(C4C(OC)=NC=C(C(C)C)C=4)=CN=C(S(C)(=O)=O)N=3)[C@H]2C)C=C(C(F)(F)F)C=1>>[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:37]4[C:33]([CH3:32])=[N:34][O:35][C:36]=4[CH3:41])=[CH:24][N:23]=[C:22]([S:27][CH3:28])[N:21]=3)[C@H:14]2[CH3:29])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

4

Reactant 3

HCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 57576287(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-{[5-bromo-2-(methylthio)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one2×HCID 90009173(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-{[5-(5-isopropyl-2-methoxypyridin-3-yl)-2-(methylsulfonyl)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

Product 1

HCID 90009160(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5-(3,5-dimethylisoxazol-4-yl)-2-(methylthio)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

Procedure

To a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5-bromo-2-(methylsulfanyl)pyrimidin-4-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (INTERMEDIATE 8, 500 mg, 0.943 mmole) and 3,5-dimethylisoxazole-4-boronic acid, pinacol ester (231 mg, 1.037 mmol) were treated in a similar fashion to INTERMEDIATE 17 Step A or EXAMPLE 64 Step A to give the title compound after filtration of the reaction mixture, evaporation and silica gel purification of the crude isolate. LCMS (M+H)+: 547.2.

Sources & evidence

ORD record
ord-6a2e004224b344cea4b01f223df23b68
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

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