1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-[(4'-tert-Butylbiphenyl-2-carbonyl)amino]quinoline-6-carboxylic acid benzyl ester

HRID 746986ノート

反応式

HRID 746986 の反応式
[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[C:16]([NH2:21])[CH:15]=[CH:14]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[C:33]([C:38](O)=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1.C([O-])(O)=O.[Na+]>[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[C:16]([NH:21][C:38]([C:33]1[C:32]([C:29]3[CH:28]=[CH:27][C:26]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:31][CH:30]=3)=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:39])[CH:15]=[CH:14]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11414765Benzyl 2-aminoquinoline-6-carboxylateHCID 136292864'-(tert-Butyl)-[1,1'-biphenyl]-2-carboxylic acid

生成物 1

HCID 597109932-[(4'-tert-Butylbiphenyl-2-carbonyl)amino]quinoline-6-carboxylic acid benzyl ester収率 79.4%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To solution of 2-aminoquinoline-6-carboxylic acid benzyl ester (25 g, 100 mmol) and 4′-tert-butylbiphenyl-2-carboxylic acid (19.5 g, 70 mmol) in CH2Cl2 (500 mL) was added 4-dimethylaminopyridine (9.77 g, 80 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (19.2 g, 100 mmol). The reaction mixture was stirred at room temperature for 18 h and then diluted with saturated aqueous NaHCO3 solution. The aqueous phase was separated and extracted with CH2Cl2. Combined organic layers were washed with brine, dried over MgSO4 and concentrated. The title compound (28.6 g, 79%) was isolated by column chromatography eluting with a gradient of 5% to 30% EtOAc in hexane.

後処理

  1. customThe aqueous phase was separated
  2. extractionextracted with CH2Cl2
  3. washCombined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-e6ad6b5fbc9e4879867993914f2c4ab5
出典データセット
uspto-grants-2008_07
特許番号
US07393958B2

反応ノート

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