Dimethylformamide → 2'-Fluoro-5-(5-methyl-pyridin-2-yl)-6'-trifluoromethyl-biphenyl-3-carboxylic acid ((R)-1-methyl-2-morpholin-4-yl-ethyl)-amide

HRID 2278763Notes

Reaction equation

HRID 2278763 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=2)[CH:15]=[C:14]([C:25]([OH:27])=O)[CH:13]=1.Cl.[O:29]1[CH2:34][CH2:33][N:32]([CH2:35][C@@H:36]([NH2:38])[CH3:37])[CH2:31][CH2:30]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>>[CH3:37][C@@H:36]([NH:38][C:25]([C:14]1[CH:13]=[C:12]([C:3]2[C:4]([C:8]([F:9])([F:10])[F:11])=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=2)[CH:15]=1)=[O:27])[CH2:35][N:32]1[CH2:33][CH2:34][O:29][CH2:30][CH2:31]1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 673043082'-Fluoro-5-(5-methylpyridin-2-yl)-6'-(trifluoromethyl)biphenyl-3-carboxylic acidHCID 67387737(S)-1-Morpholinopropan-2-amine hydrochloride

Product 1

HCID 451385492'-Fluoro-5-(5-methyl-pyridin-2-yl)-6'-trifluoromethyl-biphenyl-3-carboxylic acid ((R)-1-methyl-2-morpholin-4-yl-ethyl)-amide

Procedure

A round bottom flask was charged with 2′-fluoro-5-(5-methylpyridin-2-yl)-6′-(trifluoromethyl)biphenyl-3-carboxylic acid (100.00 mg, 0.26644 mmol), (S)-1-morpholinopropan-2-amine hydrochloride (112.10 mg, 0.62047 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.49150 g, 1.2926 mmol), N,N-diisopropylethylamine (0.36025 mL, 2.0682 mmol), N,N-dimethylformamide (0.882 mL, 11.4 mmol) and the reaction stirred over night at room temperature. The solvent was removed under reduced pressure and the residue purified by prep HPLC to get the compound as white solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by prep HPLC

Sources & evidence

ORD record
ord-3da76e04e2c9422b894023fc7bb91f22
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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