Diisopropylethylamine → (R)-2'-cyano-5-(5-methylpyridin-2-yl)-N-(1-morpholinopropan-2-yl)-5'-(trifluoromethyl)biphenyl-3-carboxamide

HRID 2278760Notes

Reaction equation

HRID 2278760 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[C:13]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=2)[CH:16]=[C:15]([C:26]([OH:28])=O)[CH:14]=1)#[N:2].Cl.[O:30]1[CH2:35][CH2:34][N:33]([CH2:36][C@H:37]([NH2:39])[CH3:38])[CH2:32][CH2:31]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>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:10])[F:11])=[CH:5][C:4]=1[C:13]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=2)[CH:16]=[C:15]([C:26]([NH:39][C@H:37]([CH3:38])[CH2:36][N:33]2[CH2:34][CH2:35][O:30][CH2:31][CH2:32]2)=[O:28])[CH:14]=1)#[N:2]

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 584493572'-Cyano-5-(5-methylpyridin-2-yl)-5'-(trifluoromethyl)biphenyl-3-carboxylic acidHCID 67310127(R)-1-Morpholinopropan-2-amine hydrochloride

Product 1

HCID 45138403(R)-2'-cyano-5-(5-methylpyridin-2-yl)-N-(1-morpholinopropan-2-yl)-5'-(trifluoromethyl)biphenyl-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A round bottom flask was charged with 2′-cyano-5-(5-methylpyridin-2-yl)-5′-(trifluoromethyl)biphenyl-3-carboxylic acid (30 mg, 0.078 mmol), (R)-1-morpholinopropan-2-amine hydrochloride (33 mg, 0.18 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (145 mg, 0.38 mmol), N,N-diisopropylethylamine (106 μL, 0.61 mmol), N,N-dimethylformamide (0.5 mL) and the reaction was stirred overnight at room temperature. The mixture was purified by HPLC to afford the title compound as a light orange solid.

Workup

  1. customThe mixture was purified by HPLC

Sources & evidence

ORD record
ord-a1860328373b4d32a2b725e91e59f635
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

Loading…