1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Tert-butyl 4-{[7-({[3-cyano-5-(trifluoromethyl)phenyl]-amino}carbonyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}pyridine-2-carboxylate

HRID 1640185노트

반응식

HRID 1640185 반응식
[C:1]([O:5][C:6]([C:8]1[CH:13]=[C:12]([O:14][C:15]2[CH:24]=[C:23]3[C:18]([CH2:19][CH2:20][CH:21]([C:25](O)=[O:26])[CH2:22]3)=[CH:17][CH:16]=2)[CH:11]=[CH:10][N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:28][C:29]1[CH:30]=[C:31]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[C:32]#[N:33].CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl.CCOC(C)=O>[C:32]([C:31]1[CH:30]=[C:29]([NH:28][C:25]([CH:21]2[CH2:22][C:23]3[CH:24]=[C:15]([O:14][C:12]4[CH:11]=[CH:10][N:9]=[C:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:13]=4)[CH:16]=[CH:17][C:18]=3[CH2:19][CH2:20]2)=[O:26])[CH:36]=[C:35]([C:37]([F:38])([F:39])[F:40])[CH:34]=1)#[N:33]

참가 물질

7

반응물 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 225022643-Amino-5-(trifluoromethyl)benzonitrileHCID 589023357-{[2-(Tert-butoxycarbonyl)pyridin-4-yl]oxy}-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

생성물 1

HCID 58902379Tert-butyl 4-{[7-({[3-cyano-5-(trifluoromethyl)phenyl]-amino}carbonyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}pyridine-2-carboxylate수율 79%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 7-{[2-(tert-butoxycarbonyl)pyridin-4-yl]oxy}-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (0.653 g, 1.77 mmol), 3-amino-5-(trifluoromethyl)-benzonitrile (0.362 g, 1.94 mmol), and DMAP (0.238 g, 1.94 mmol) in DCM (10 mL) was cooled to 0° C. To this solution was added EDCI (0.339 g, 1.77 mmol). The reaction mixture was allowed to stir and warm to rt overnight. The reaction mixture was diluted with EtOAc, washed with 1N HCl and sat. aq. NaHCO3, and concentrated. The residue was purified by column chromatography to give tert-butyl 4-{[7-({[3-cyano-5-(trifluoromethyl)phenyl]-amino}carbonyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}pyridine-2-carboxylate (0.750 g, 79%). LCMS: (FA) ES+ 538.6.

후처리

  1. washwashed with 1N HCl and sat. aq. NaHCO3
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-cc19c1e1557448c9b326a5e6685ca7bd
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110687B2

반응 노트

불러오는 중…