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

HRID 1845198노트

반응식

HRID 1845198 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-9158514821af4b0788793178e4ff151f
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

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