Diisopropylethylamine → 4'-Methyl-N-((2-methylpyrimidin-5-yl)methyl)-5-(methylsulfonyl)biphenyl-3-carboxamide

HRID 1845176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845176
[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.[CH3:44][C:45]1[N:50]=[CH:49][C:48]([CH2:51][NH2:52])=[CH:47][N:46]=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:52][CH2:51][C:48]3[CH:47]=[N:46][C:45]([CH3:44])=[N:50][CH:49]=3)=[O:20])[CH:9]=2)=[CH:6][CH:7]=1

Komponenten

7

Edukt 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21294601(2-Methylpyrimidin-5-yl)methanamineHCID 581879934'-Methyl-5-(methylsulfonyl)biphenyl-3-carboxylic acid

Produkt 1

HCID 581879694'-Methyl-N-((2-methylpyrimidin-5-yl)methyl)-5-(methylsulfonyl)biphenyl-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 4′-methyl-5-(methylsulfonyl)biphenyl-3-carboxylic acid (45 mg, 0.15 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (59 mg, 0.31 mmol), 1-hydroxybenzotriazole hydrate (24 mg, 0.15 mmol), and CH2Cl2 (3 mL) were added (2-methylpyrimidin-5-yl)methanamine (29 mg, 0.23 mmol) and N,N-diisopropylethylamine (54 μL, 0.31 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; 30-60% MeCN-water[10 mM Et2NH]) to afford a white solid.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue was purified by preparative HPLC (100×20.2 mm, C18 column; 30-60% MeCN-water[10 mM Et2NH])
  3. customto afford a white solid

Quellen und Nachweise

ORD-Eintrag
ord-d4b29b749fb141e5be0953ed7bf664f0
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946439B2

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