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

HRID 239982

반응식

HRID 239982 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6f0ea8d061d54ba3b40e3ef34ccef83c
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642768B2

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