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

HRID 2278759Notes

Reaction equation

HRID 2278759 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=2)[CH:12]=[C:11]([C:22](O)=[O:23])[CH:10]=1.Cl.[O:26]1[CH2:31][CH2:30][N:29]([CH2:32][C@H:33]([NH2:35])[CH3:34])[CH2:28][CH2:27]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>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=2)[CH:12]=[C:11]([C:22]([NH:35][C@H:33]([CH3:34])[CH2:32][N:29]2[CH2:30][CH2:31][O:26][CH2:27][CH2:28]2)=[O:23])[CH:10]=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 584493602',3'-Difluoro-5-(5-methylpyridin-2-yl)biphenyl-3-carboxylic acidHCID 67310127(R)-1-Morpholinopropan-2-amine hydrochloride

Product 1

HCID 45138400(R)-2',3'-difluoro-5-(5-methylpyridin-2-yl)-N-(1-morpholinopropan-2-yl)biphenyl-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A round bottom flask was charged with 2′,3′-difluoro-5-(5-methylpyridin-2-yl)biphenyl-3-carboxylic acid (30 mg, 0.092 mmol), (R)-1-morpholinopropan-2-amine hydrochloride (20 mg, 0.11 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (88 mg, 0.23 mmol), N,N-diisopropylethylamine (64 μL, 0.37 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-d7e385d7f3464226bb8a7d374d415a08
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

Loading…