Trifluoroacetic acid → 5-[3-(cyanomethyl)-3-[3-methyl-4-(1H-pyrazol-4-yl)pyrazol-1-yl]azetidin-1-yl]-N-propan-2-ylpyrazine-2-carboxamide;2,2,2-trifluoroacetic acid
Reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].Br[C:9]1[CH:10]=[N:11][N:12](C(OC(C)(C)C)=O)[CH:13]=1.[C:21]([CH2:23][C:24]1([N:40]2[CH:44]=[C:43](B3OC(C)(C)C(C)(C)O3)[C:42]([CH3:54])=[N:41]2)[CH2:27][N:26]([C:28]2[N:29]=[CH:30][C:31]([C:34]([NH:36][CH:37]([CH3:39])[CH3:38])=[O:35])=[N:32][CH:33]=2)[CH2:25]1)#[N:22]>>[F:4][C:3]([F:6])([F:5])[C:1]([OH:7])=[O:2].[C:21]([CH2:23][C:24]1([N:40]2[CH:44]=[C:43]([C:9]3[CH:10]=[N:11][NH:12][CH:13]=3)[C:42]([CH3:54])=[N:41]2)[CH2:25][N:26]([C:28]2[N:29]=[CH:30][C:31]([C:34]([NH:36][CH:37]([CH3:38])[CH3:39])=[O:35])=[N:32][CH:33]=2)[CH2:27]1)#[N:22]Participants
4
Reactant 3
Product 1
Procedure
This compound was prepared as TFA salt by using procedures analogous to those described for the synthesis of Example 4, Step 6 starting from tert-butyl 4-bromo-1H-pyrazole-1-carboxylate and 5-{3-(cyanomethyl)-3-[3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-isopropylpyrazine-2-carboxamide. LCMS calculated for C20H24N9O (M+1)+: m/z=406.2. Found: 406.1.
Sources & evidence
- ORD record
- ord-e802c0bfc5f941d499c19685a108a238
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382231B2
Reaction notes
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