Diisopropylethylamine → (R)-2,4'-Dimethyl-N-(1-(2-methylpyrimidin-5-yl)ethyl)-5-(pyrrolidin-1-ylsulfonyl)biphenyl-3-carboxamide
Reaction equation
[CH3:1][C:2]1[C:7]([C:8](O)=[O:9])=[CH:6][C:5]([S:11]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:4][C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1.[CH3:26][C:27]1[N:32]=[CH:31][C:30]([C@H:33]([NH2:35])[CH3:34])=[CH:29][N:28]=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>[CH3:1][C:2]1[C:7]([C:8]([NH:35][C@@H:33]([C:30]2[CH:29]=[N:28][C:27]([CH3:26])=[N:32][CH:31]=2)[CH3:34])=[O:9])=[CH:6][C:5]([S:11]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:4][C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=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 55281681(R)-1-(2-Methyl-5-pyrimidinyl)ethanamine
HCID 581880832,4'-Dimethyl-5-(pyrrolidin-1-ylsulfonyl)biphenyl-3-carboxylic acidProduct 1
Reagents, catalysts & solvents 1
Procedure
A reaction vial was charged with 2,4′-dimethyl-5-(pyrrolidin-1-ylsulfonyl)biphenyl-3-carboxylic acid (40 mg, 0.11 mmol), (R)-1-(2-methylpyrimidin-5-yl)ethanamine (20 mg, 0.14 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (106 mg, 0.28 mmol), N,N-diisopropylethylamine (39 μL, 0.22 mmol) and N,N-dimethylformamide (1.33 mL), and the reaction mixture was stirred at room temperature overnight. The reaction mixture was purified by preparative HPLC to afford the compound as a light brown solid.
Workup
- customA reaction
- customThe reaction mixture was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-5707546059a84bf5a6f812d9ac6c7707
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946439B2
Reaction notes
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