Cyclopropanecarbonyl chloride → Cyclopropanecarboxylic acid [2-(2-methoxy-benzylamino)-quinolin-6-yl]-amide

HRID 1803084ノート

反応式

HRID 1803084 の反応式
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH2:17])[CH:13]=2)[N:8]=1.[CH:22]1([C:25](Cl)=[O:26])[CH2:24][CH2:23]1>C(#N)C.C(=O)(O)[O-].[Na+].O>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:17][C:25]([CH:22]3[CH2:24][CH2:23]3)=[O:26])[CH:13]=2)[N:8]=1

参加物

6

反応物 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 43450845N2-(2-Methoxy-benzyl)-quinoline-2,6-diamine

生成物 1

HCID 44223161Cyclopropanecarboxylic acid [2-(2-methoxy-benzylamino)-quinolin-6-yl]-amide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

N2-(2-Methoxy-benzyl)-quinoline-2,6-diamine (example 10, step B, 150 mg, 0.537 mmol) was dissolved in 6 mL acetonitrile and 6 mL saturated sodium bicarbonate solution. Cyclopropane carbonyl chloride (63 mg, 0.60 mmol) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with 50 mL water and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with water (30 ml), dried with sodium sulfate and evaporated. The crude product was recrystallized from diisopropyl ether. The title compound was obtained as a white solid (123 mg, 66%), MS: m/e=348.3 (M+H+).

後処理

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. washThe combined organic layers were washed with water (30 ml)
  3. dry with materialdried with sodium sulfate
  4. customevaporated
  5. customThe crude product was recrystallized from diisopropyl ether

出典と根拠

ORDレコード
ord-b43b41d1067a4f989da324ea04306c4e
出典データセット
uspto-grants-2013_01
特許番号
US08350028B2

反応ノート

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