Diisopropylethylamine → (R)-4'-Methyl-N-(1-(6-methylpyridin-3-yl)ethyl)-5-(pyrimidin-2-yloxy)biphenyl-3-carboxamide

HRID 1845266Notes

Reaction equation

HRID 1845266 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[N:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:11]=[C:10]([C:21]([OH:23])=O)[CH:9]=2)=[CH:4][CH:3]=1.Cl.Cl.[CH3:26][C:27]1[N:32]=[CH:31][C:30]([C@H:33]([NH2:35])[CH3:34])=[CH:29][CH: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[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[N:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:11]=[C:10]([C:21]([NH:35][C@@H:33]([C:30]3[CH:31]=[N:32][C:27]([CH3:26])=[CH:28][CH:29]=3)[CH3:34])=[O:23])[CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 581880344'-Methyl-5-(pyrimidin-2-yloxy)biphenyl-3-carboxylic acidHCID 67053782(R)-1-(6-Methylpyridin-3-yl)ethan-1-amine dihydrochloride

Product 1

HCID 58188241(R)-4'-Methyl-N-(1-(6-methylpyridin-3-yl)ethyl)-5-(pyrimidin-2-yloxy)biphenyl-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4′-methyl-5-(pyrimidin-2-yloxy)biphenyl-3-carboxylic acid (20 mg, 0.065 mmol) in N,N-dimethylformamide (1 mL) were added (R)-1-(6-methylpyridin-3-yl)ethanamine dihydrochloride (30 mg, 0.143 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (60 mg, 0.16 mmol), and N,N-diisopropylethylamine (200 μL, 1.15 mmol). The reaction mixture was stirred at room temperature for 16 hours. LC-MS indicated the reaction was complete. The reaction mixture was purified by preparative HPLC (100×21.2 mm C18 column, CH3CN/water[10 mM Et2NH]) to afford a light color solid.

Workup

  1. customThe reaction mixture was purified by preparative HPLC (100×21.2 mm C18 column, CH3CN/water[10 mM Et2NH])
  2. customto afford a light color solid

Sources & evidence

ORD record
ord-30489d44cbcd411fa2b3641306d29216
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

Loading…