3-Chloro-4-(3-fluorobenzyloxy)aniline → N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine

HRID 1787019노트

반응식

HRID 1787019 반응식
Cl[C:2]1[C:3]2[N:10]([CH2:11][CH2:12][CH2:13][Cl:14])[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=1)[NH2:19]>C(O)(C)C>[Cl:15][C:16]1[CH:17]=[C:18]([NH:19][C:2]2[C:3]3[N:10]([CH2:11][CH2:12][CH2:13][Cl:14])[CH:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:20]=[CH:21][C:22]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=1

참가 물질

4

반응물 2

HCID 70592633-Chloro-4-(3-fluorobenzyloxy)anilineHCID 860848304-chloro-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidine

생성물 1

HCID 67520636N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine수율 73.3%

시약·촉매·용매 1

HCID 3776Isopropanol용매

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온도
80 °C

실험 절차

A mixture of 4-chloro-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidine (839 mg), 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (1.10 g) and isopropyl alcohol (5 mL) was stirred at 80° C. for 1.5 hrs. The mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate (30 mL) was added to the residue, and the mixture was extracted with ethyl acetate (30 mL×3). The organic layers were combined, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=90:10→20:80) to give the title compound (1.19 g).

후처리

  1. concentrationThe mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate (30 mL)
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate (30 mL×3)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=90:10→20:80)

출처 및 근거

ORD 기록
ord-91dc9102b7f34636ba1dcb54a14af106
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07507740B2

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