1-Hydroxybenzotriazole → 2'-Cyano-4'-methyl-5-(pyrrolidine-1-carbonyl)-N-((6-(trifluoromethyl)pyridin-3-yl)methyl)biphenyl-3-carboxamide

HRID 1845198ノート

反応式

HRID 1845198 の反応式
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])[CH:13]=[C:12]([C:23](O)=[O:24])[CH:11]=1)#[N:2].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[F:57][C:58]([F:68])([F:67])[C:59]1[N:64]=[CH:63][C:62]([CH2:65][NH2:66])=[CH:61][CH:60]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]([N:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)=[O:17])[CH:13]=[C:12]([C:23]([NH:66][CH2:65][C:62]2[CH:63]=[N:64][C:59]([C:58]([F:68])([F:57])[F:67])=[CH:60][CH:61]=2)=[O:24])[CH:11]=1)#[N:2]

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27377185-(Aminomethyl)-2-(trifluoromethyl)pyridineHCID 581881162'-Cyano-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acid

生成物 1

HCID 581881742'-Cyano-4'-methyl-5-(pyrrolidine-1-carbonyl)-N-((6-(trifluoromethyl)pyridin-3-yl)methyl)biphenyl-3-carboxamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A round-bottom flask was charged with 2′-cyano-4′-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylic acid (50 mg, 0.1 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (52 mg, 0.27 mmol), 1-hydroxybenzotriazole (36 mg, 0.27 mmol), N,N-diisopropylethylamine (35 mg, 0.27 mmol), methylene chloride (4 mL), 4-dimethylaminopyridine (1 mg), and C-(6-trifluoromethyl-pyridin-3-yl)-methylamine (47 mg, 0.27 mmol). The mixture was stirred at room temperature overnight, and then diluted with CH2Cl2, washed with aq. Na2HPO4, brine, and dried over Na2SO4, and concentrated. The residue was purified via preparative HPLC to afford the desired product as a white solid.

後処理

  1. washwashed with aq. Na2HPO4, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified via preparative HPLC

出典と根拠

ORDレコード
ord-9158514821af4b0788793178e4ff151f
出典データセット
uspto-grants-2015_02
特許番号
US08946439B2

反応ノート

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