HCID 67034444, compound → HCID 178519149, compound

HRID 539092Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:13][O:12][C:11](=[O:14])[N:10]2[C:15]2[CH:20]=[CH:19][N:18]3[N:21]=[CH:22][C:23]([C:24]4[CH:29]=[CH:28][C:27]([C:30]5[N:34]=[CH:33][N:32](COCC[Si](C)(C)C)[N:31]=5)=[C:26]([F:43])[CH:25]=4)=[C:17]3[N:16]=2)[CH:5]=[CH:6][C:7]=1[F:8].FC1C=C([C@H]2COC(=O)N2C2C=CN3N=CC(C4C=CC(C5N(COCC[Si](C)(C)C)N=CN=5)=C(F)C=4)=C3N=2)C=CC=1F>>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:13][O:12][C:11](=[O:14])[N:10]2[C:15]2[CH:20]=[CH:19][N:18]3[N:21]=[CH:22][C:23]([C:24]4[CH:29]=[CH:28][C:27]([C:30]5[N:34]=[CH:33][NH:32][N:31]=5)=[C:26]([F:43])[CH:25]=4)=[C:17]3[N:16]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Reactant 2

HCID 67034444HCID 67034444, compound

HCID 67036085HCID 67036085, compound

Product 1

HCID 178519149HCID 178519149, compoundYield 73%

Procedure

(S)-4-(3,4-difluorophenyl)-3-(3-(3-fluoro-4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one (30 mg, 73%) was prepared by the procedure described in Example 1, Step 9, using a mixture of (S)-4-(3,4-difluorophenyl)-3-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one and (S)-4-(3,4-difluorophenyl)-3-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-5-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one. LCMS (APCI+) m/z 478.2 [M+H]+.

Sources & evidence

ORD record: ord-8ccf9b9934b047698acbd803ace69de3
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865726B2

Reaction notes

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