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

HRID 1803084

반응식

HRID 1803084 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 516892Sodium Bicarbonate용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-b43b41d1067a4f989da324ea04306c4e
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08350028B2

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