Trifluoroacetic acid → HCID 178525672, compound

HRID 539048Notes

Reaction equation

HRID 539048 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:13]=[N:14][N:15]4[CH:20]=[CH:19][C:18]([N:21]5[CH2:25][CH:24]([C:26]([F:29])([F:28])[F:27])[O:23][C:22]5=[O:30])=[N:17][C:16]=34)=[CH:8][CH:7]=2)=[N:2]1.[C:31]([OH:37])([C:33]([F:36])([F:35])[F:34])=[O:32].FC(F)(F)C1OC(=O)NC1.CC1(C)C(C)(C)OB(C2C=CC(C3N(COCC[Si](C)(C)C)C=CN=3)=CC=2)O1>>[F:34][C:33]([F:36])([F:35])[C:31]([OH:37])=[O:32].[NH:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[CH:13]=[N:14][N:15]4[CH:20]=[CH:19][C:18]([N:21]5[CH2:25][CH:24]([C:26]([F:29])([F:28])[F:27])[O:23][C:22]5=[O:30])=[N:17][C:16]=34)=[CH:10][CH:11]=2)=[N:2]1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 136496485-(Trifluoromethyl)oxazolidin-2-oneHCID 670343202-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazoleHCID 1785191353-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-5-(trifluoromethyl)oxazolidin-2-one

Product 1

HCID 178525672HCID 178525672, compound

Procedure

3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-5-(trifluoromethyl)oxazolidin-2-one (3.3 mg, 10%) as the TFA salt was made from 5-(trifluoromethyl)oxazolidin-2-one according to the method of Example 1, Step 4, and substituting 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-((2-(trimethylsilyl) ethoxy)methyl)-1H-1,2,4-triazole for 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole in Example 1, Step 8. LCMS (APCI+) m/z 416 [M+H]+.

Sources & evidence

ORD record
ord-f8745d8f31a3489fa58f0d1c2fe0ee1c
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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