Diisopropylethylamine → 5-(3-Hydroxyazetidine-1-carbonyl)-4'-methyl-N-((6-(trifluoromethyl)pyridin-3-yl)methyl)biphenyl-3-carboxamide
Reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([C:8]2[CH:9]=[C:10]([C:21](O)=[O:22])[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)[CH:13]=2)=[O:7])[CH2:3]1.[F:24][C:25]([F:35])([F:34])[C:26]1[N:31]=[CH:30][C:29]([CH2:32][NH2:33])=[CH:28][CH:27]=1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[OH:1][CH:2]1[CH2:5][N:4]([C:6]([C:8]2[CH:9]=[C:10]([C:21]([NH:33][CH2:32][C:29]3[CH:30]=[N:31][C:26]([C:25]([F:35])([F:24])[F:34])=[CH:27][CH:28]=3)=[O:22])[CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=3)[CH:13]=2)=[O:7])[CH2:3]1Participants
6
Reactant 4
HCID 81531Diisopropylethylamine
HCID 27377185-(Aminomethyl)-2-(trifluoromethyl)pyridine
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 581883575-(3-Hydroxyazetidine-1-carbonyl)-4'-methylbiphenyl-3-carboxylic acidProduct 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 5-(3-hydroxyazetidine-1-carbonyl)-4′-methylbiphenyl-3-carboxylic acid (80 mg, 0.26 mmol) in N,N-dimethylformamide (1.5 mL) were added C-(6-trifluoromethyl-pyridin-3-yl)-methylamine (70 mg, 0.40 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (200 mg, 0.53 mmol), and N,N-diisopropylethylamine (200 pt, 1.15 mmol). The reaction mixture was stirred for 16 hours at 25° C. The reaction mixture was purified by preparative HPLC to afford a white solid.
Workup
- customThe reaction mixture was purified by preparative HPLC
- customto afford a white solid
Sources & evidence
- ORD record
- ord-67e6e2a1c3db41bc9a2700cb2e671b51
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946439B2
Reaction notes
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