Reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:25][C:26]1[C:27]([OH:35])=[N:28][CH:29]=[C:30]([CH:34]=1)[C:31]([OH:33])=O.CCN(C(C)C)C(C)C.Cl.[F:46][C:47]1[C:48]([C@H:53]([C:55]2[CH:60]=[CH:59][C:58]([C:61]([F:64])([F:63])[F:62])=[CH:57][CH:56]=2)[NH2:54])=[N:49][CH:50]=[CH:51][CH:52]=1.Cl.FC(F)(F)C1C=CC([C@@H](C2C(C(F)(F)F)=CC=CN=2)N)=CC=1>C(Cl)Cl>[Br:25][C:26]1[C:27](=[O:35])[NH:28][CH:29]=[C:30]([C:31]([NH:54][C@H:53]([C:48]2[C:47]([F:46])=[CH:52][CH:51]=[CH:50][N:49]=2)[C:55]2[CH:60]=[CH:59][C:58]([C:61]([F:62])([F:63])[F:64])=[CH:57][CH:56]=2)=[O:33])[CH:34]=1Participants
7
Reactant 5
HCID 81531Diisopropylethylamine
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 71144279(S)-(3-Fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methanamine Hydrochloride
HCID 86687962(S)-(4-(Trifluoromethyl)phenyl)(3-(trifluoromethyl)pyridin-2-yl)methanamine Hydrochloride
HCID 178524767HCID 178524767, compoundProduct 1
Reagents, catalysts & solvents 1
Procedure
To a solution of HATU (0.332 g, 0.874 mmol) in DCM (2 mL) was added 5-bromo-6-hydroxynicotinic acid (0.191 g, 0.874 mmol) and DIPEA (0.406 mL, 2.331 mmol). The resulting mixture was then stirred at rt for 5 min, then (S)-(3-fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methanamine hydrochloride (Intermediate 2) (0.200 g, 0.583 mmol) was added. The mixture was then stirred at rt overnight. The mixture was purified by silica gel column chromatography using an ISCO instrument (0%-100% EtOAc/hexane) to give the title compound as a brown oil.
Workup
- stirringThe mixture was then stirred at rt overnight
- customThe mixture was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-150594b0a7c149ebbebd15c546682185
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710043B2
Linked notes
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