Diisopropylethylamine → N-((2'-fluoro-3-methyl-2,4'-bipyridin-5-yl)methyl)-5-(3-fluorophenyl)picolinamide
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([OH:16])=O)=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[F:17][C:18]1[CH:23]=[C:22]([C:24]2[C:29]([CH3:30])=[CH:28][C:27]([CH2:31][NH2:32])=[CH:26][N:25]=2)[CH:21]=[CH:20][N:19]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C.CS(C)=O>[F:17][C:18]1[CH:23]=[C:22]([C:24]2[C:29]([CH3:30])=[CH:28][C:27]([CH2:31][NH:32][C:14](=[O:16])[C:11]3[CH:10]=[CH:9][C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=4)=[CH:13][N:12]=3)=[CH:26][N:25]=2)[CH:21]=[CH:20][N:19]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a mixture of 5-(3-fluorophenyl)picolinic acid 6-7 (32 mg, 0.15 mmol), (2′-fluoro-3-methyl-2,4′-bipyridin-5-yl)methanamine 30-5 (28 mg, 0.13 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU) (60 mg, 0.16 mmol) in DMF (1.0 mL) was added DIEA (0.068 mL, 0.39 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted into DMSO and purified by HPLC to give N-((2′-fluoro-3-methyl-2,4′-bipyridin-5-yl)methyl)-5-(3-fluorophenyl)picolinamide 30 as a white solid. MS m/z 417.2 (M+1). 1H NMR 400 MHz (DMSO-d6) δ 9.54 (t, 1H), 8.95 (dd, 1H), 8.47 (d, 1H), 8.29 (m, 2H), 8.07 (dd, 1H), 7.69 (m, 2H), 7.63 (m, 1H), 7.55 (m, 1H), 7.48 (m, 1H), 7.29 (m, 2H), 4.52 (d, 2H), 2.28 (s, 3H).
Workup
- custompurified by HPLC
Sources & evidence
- ORD record
- ord-3be738d77e5f408b9e04e3c0d62088cf
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181235B2
Reaction notes
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