Diisopropylethylamine → Methyl 4-[(2-chloroquinoline-4-carbonyl)amino]-3,5-dimethyl-benzoate

HRID 239978

反応式

HRID 239978 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:25]([CH3:26])=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[CH3:27].C(N(CC)C(C)C)(C)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])=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][C:25]=2[CH3:26])=[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 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 2305822-Chloroquinoline-4-carboxylic acidHCID 11030398Benzoic acid, 4-amino-3,5-dimethyl-, methyl ester

生成物 1

HCID 86707363Methyl 4-[(2-chloroquinoline-4-carbonyl)amino]-3,5-dimethyl-benzoate収率 960.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
40 °C

実験手順

To a solution of 2-chloroquinoline-4-carboxylic acid (5.00 g, 0.0024 mol) in CH2Cl2 (50 mL) at 0° C. are added methyl 4-amino-3,5-dimethylbenzoate (3.88 g, 0.02167 mol, see preparation 12) and N,N-diisopropylethylamine (12.5 ml, 0.07225 mol). After stirring the reaction mixture for 10 minutes, 1-propanephosphonic acid cyclic anhydride (50% solution in ethyl acetate, 31.0 ml, 0.048 mol) is added via syringe and heated at 40° C. After 5 hours, the reaction mixture is diluted with water and extracted with dichloromethane. The organic layers are combined and dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (silica gel) using a gradient of 0-40% ethyl acetate in hexanes. After purification the solid is triturated with 20% diethyl ether in pentane and dried to give the title compound as a white solid (8.50 g, 96%). Mass spectrum (m/z): 369.1 (M+1).

後処理

  1. waitAfter 5 hours
  2. extractionextracted with dichloromethane
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by flash chromatography (silica gel)
  7. customAfter purification the solid
  8. customis triturated with 20% diethyl ether in pentane
  9. customdried

出典と根拠

ORDレコード
ord-543cff2aef534d55add2ec8d683941a5
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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