6-Fluoronicotinic Acid → HCID 58487798, compound
Reaction equation
CN([C:4]([O:8]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[F:23][C:24]1[CH:32]=[CH:31][C:27](C(O)=O)=[CH:26][N:25]=1.FC(F)(F)C(O)=O.[CH3:40][O:41][C:42]1[CH:62]=[CH:61][C:45]([O:46][C:47]2[CH:60]=[CH:59][C:50]([CH2:51][NH:52][C:53]([C:55]3([NH2:58])[CH2:57][CH2:56]3)=[O:54])=[CH:49][CH:48]=2)=[C:44]([C:63]([F:66])([F:65])[F:64])[CH:43]=1>CN(C=O)C>[F:23][C:24]1[CH:32]=[C:31]([CH:27]=[CH:26][N:25]=1)[C:4]([NH:58][C:55]1([C:53](=[O:54])[NH:52][CH2:51][C:50]2[CH:59]=[CH:60][C:47]([O:46][C:45]3[CH:61]=[CH:62][C:42]([O:41][CH3:40])=[CH:43][C:44]=3[C:63]([F:64])([F:65])[F:66])=[CH:48][CH:49]=2)[CH2:56][CH2:57]1)=[O:8]Participants
5
Procedure
68 μL (0.48 mmol) of TEA and 57 mg (0.19 mmol) of TBTU were added to a solution of 23 mg (0.16 mmol) of 6-fluoro-nicotinic acid in 2 mL DMF and the mixture was stirred for 5 min at RT. Then 80 mg (0.16 mmol) of 1-amino-cyclopropanecarboxylic acid 4-(4-methoxy-2-trifluoromethyl-phenoxy)-benzylamide-trifluoroacetic acid salt (from 85a) was added and the mixture was stirred for 2 h at ambient temperature. A further 57 mg (0.19 mmol) of TBTU, 68 μL (0.48 mmol) of TEA and 23 mg (0.16 mmol) of 6-fluoro-nicotinic acid were added and the mixture was stirred overnight at RT. The reaction mixture was purified by chromatography (reversed phase).
Workup
- stirringthe mixture was stirred for 2 h at ambient temperature
- stirringthe mixture was stirred overnight at RT
- customThe reaction mixture was purified by chromatography (reversed phase)
Sources & evidence
- ORD record
- ord-cbbd79bc448b4de3a6032d6a4004baca
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916589B2
Reaction notes
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