Diisopropylethylamine → 5-(Hydroxy(phenyl)methyl)-4'-methyl-N-((R)-1-(6-methylpyridin-3-yl)ethyl)biphenyl-3-carboxamide
Reaction equation
[OH:1][CH:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:3]1[CH:4]=[C:5]([C:16](O)=[O:17])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:8]=1.Cl.Cl.[CH3:27][C:28]1[N:33]=[CH:32][C:31]([C@H:34]([NH2:36])[CH3:35])=[CH:30][CH:29]=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]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:3]1[CH:4]=[C:5]([C:16]([NH:36][C@@H:34]([C:31]2[CH:32]=[N:33][C:28]([CH3:27])=[CH:29][CH:30]=2)[CH3:35])=[O:17])[CH:6]=[C:7]([C:9]2[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=2)[CH:8]=1Participants
6
Reactant 4
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 581879845-(Hydroxy(phenyl)methyl)-4'-methylbiphenyl-3-carboxylic acid
HCID 67053782(R)-1-(6-Methylpyridin-3-yl)ethan-1-amine dihydrochlorideProduct 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
To a solution of 5-(hydroxy(phenyl)methyl)-4′-methylbiphenyl-3-carboxylic acid (50 mg, 0.16 mmol) in N,N-dimethylformamide (1 mL) were added (R)-1-(6-methylpyridin-3-yl)ethanamine dihydrochloride (70 mg, 0.34 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (120 mg, 0.32 mmol) and N,N-diisopropylethylamine (500 μL, 2.87 mmol). The reaction mixture was stirred for 16 hours at 30° C. The reaction mixture was purified by preparative HPLC (100×21.2 mm C18 column, CH3CN/water[1 mM Et2NH]) to afford a light color solid.
Workup
- customThe reaction mixture was purified by preparative HPLC (100×21.2 mm C18 column, CH3CN/water[1 mM Et2NH])
- customto afford a light color solid
Sources & evidence
- ORD record
- ord-1f3a2e2dcc8d43d3b76dfcef64c16977
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946439B2
Reaction notes
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