Diisopropylethylamine → 4'-Methyl-5-(methylsulfonyl)-N-((6-(trifluoromethyl)pyridin-3-yl)methyl)biphenyl-3-carboxamide

HRID 1845187Notes

Reaction equation

HRID 1845187 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:11]=[C:10]([C:18]([OH:20])=O)[CH:9]=2)=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[F:44][C:45]([F:55])([F:54])[C:46]1[N:51]=[CH:50][C:49]([CH2:52][NH2:53])=[CH:48][CH:47]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[C:12]([S:14]([CH3:17])(=[O:15])=[O:16])[CH:11]=[C:10]([C:18]([NH:53][CH2:52][C:49]3[CH:50]=[N:51][C:46]([C:45]([F:55])([F:44])[F:54])=[CH:47][CH:48]=3)=[O:20])[CH:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27377185-(Aminomethyl)-2-(trifluoromethyl)pyridineHCID 27960291-Hydroxybenzotriazole hydrateHCID 581879934'-Methyl-5-(methylsulfonyl)biphenyl-3-carboxylic acid

Product 1

HCID 581882954'-Methyl-5-(methylsulfonyl)-N-((6-(trifluoromethyl)pyridin-3-yl)methyl)biphenyl-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4′-methyl-5-(methylsulfonyl)biphenyl-3-carboxylic acid (40 mg, 0.14 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (53 mg, 0.28 mmol), 1-hydroxybenzotriazole hydrate (21 mg, 0.14 mmol), and CH2Cl2 (3 mL) were added C-(6-trifluoromethyl-pyridin-3-yl)-methylamine (36 mg, 0.21 mmol) and N,N-diisopropylethylamine (48 μL, 0.28 mmol). The mixture was stirred at room temperature overnight and then concentrated. The residue was purified by preparative HPLC (100×20.2 mm, C18 column; 40-80% MeCN-water[10 mM Et2NH]) to afford a white solid.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by preparative HPLC (100×20.2 mm, C18 column; 40-80% MeCN-water[10 mM Et2NH])
  3. customto afford a white solid

Sources & evidence

ORD record
ord-0c235cd67e194ec5aabe8716bd955405
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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