Diisopropylethylamine → (R)-4'-Methyl-N-(1-(2-methylpyrimidin-5-yl)ethyl)-5-(thiazol-2-yloxy)biphenyl-3-carboxamide

HRID 1845269Notes

Reaction equation

HRID 1845269 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[S:16][CH:17]=[CH:18][N:19]=3)[CH:11]=[C:10]([C:20]([OH:22])=O)[CH:9]=2)=[CH:4][CH:3]=1.[CH3:23][C:24]1[N:29]=[CH:28][C:27]([C@H:30]([NH2:32])[CH3:31])=[CH:26][N:25]=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:3]=[CH:4][C:5]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[S:16][CH:17]=[CH:18][N:19]=3)[CH:11]=[C:10]([C:20]([NH:32][C@@H:30]([C:27]3[CH:26]=[N:25][C:24]([CH3:23])=[N:29][CH:28]=3)[CH3:31])=[O:22])[CH:9]=2)=[CH:6][CH:7]=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 55281681(R)-1-(2-Methyl-5-pyrimidinyl)ethanamineHCID 581880714'-Methyl-5-(thiazol-2-yloxy)biphenyl-3-carboxylic acid

Product 1

HCID 58188035(R)-4'-Methyl-N-(1-(2-methylpyrimidin-5-yl)ethyl)-5-(thiazol-2-yloxy)biphenyl-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4′-methyl-5-(thiazol-2-yloxy)biphenyl-3-carboxylic acid (50 mg, 0.16 mmol) in N,N-dimethylformamide (1 mL) were added (R)-1-(2-methylpyrimidin-5-yl)ethanamine (45 mg, 0.33 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (150 mg, 0.39 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-231ef48f674c4c36b3c80445fb0acabc
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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