Triethylamine → Methyl 3-[(2-chloroquinoline-4-carbonyl)amino]-2,4-dimethyl-benzoate

HRID 239982

反応式

HRID 239982 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]([OH:14])=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:15][C:16]1[C:17]([CH3:27])=[C:18]([CH:23]=[CH:24][C:25]=1[CH3:26])[C:19]([O:21][CH3:22])=[O:20].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C(Cl)Cl.O>[Cl:1][C:2]1[CH:11]=[C:10]([C:12]([NH:15][C:16]2[C:17]([CH3:27])=[C:18]([CH:23]=[CH:24][C:25]=2[CH3:26])[C:19]([O:21][CH3:22])=[O:20])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 2305822-Chloroquinoline-4-carboxylic acidHCID 66871802Methyl 3-amino-2,4-dimethylbenzoate

生成物 1

HCID 86707367Methyl 3-[(2-chloroquinoline-4-carbonyl)amino]-2,4-dimethyl-benzoate収率 87.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-chloroquinoline-4-carboxylic acid (0.40 g, 0.0019 mol) in CH2Cl2 (8 mL) at 0° C. are added methyl 3-amino-2,4-dimethylbenzoate (0.31 g, 0.0017 mol, see preparation 10) and triethylamine (0.80 ml, 0.0058 mol). After stirring the reaction mixture for 10 minutes, 1-propanephosphonic acid cyclic anhydride (50% solution in ethyl acetate, 2.45 ml, 0.0038 mol) is added via syringe and stirred at room temperature. After 16 hours, the reaction is diluted with water and extracted twice with dichloromethane. The organic layers are combined and dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue is triturated with 20% diethyl ether in pentane and filtered to give the title compound as an off-white solid (0.55 g, 77%). Mass spectrum (m/z): 369.1 (M+1).

後処理

  1. stirringstirred at room temperature
  2. waitAfter 16 hours
  3. extractionextracted twice with dichloromethane
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is triturated with 20% diethyl ether in pentane
  8. filtrationfiltered

出典と根拠

ORDレコード
ord-6f0ea8d061d54ba3b40e3ef34ccef83c
出典データセット
uspto-grants-2014_02
特許番号
US08642768B2

関連ノート

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