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 1640185ノート

反応式

HRID 1640185 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-cc19c1e1557448c9b326a5e6685ca7bd
出典データセット
uspto-grants-2012_02
特許番号
US08110687B2

反応ノート

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