3-Chloro-4-(3-fluorobenzyloxy)aniline → N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-1H-pyrazolo[4,3-d]pyrimidin-7-amine

HRID 1926042노트

반응식

HRID 1926042 반응식
CS[C:3]1[C:4]2[NH:11][N:10]=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=1)[NH2:16].Cl.N1C=CC=CC=1>CN1CCCC1=O.C(OCC)(=O)C>[Cl:12][C:13]1[CH:14]=[C:15]([NH:16][C:3]2[C:4]3[NH:11][N:10]=[CH:9][C:5]=3[N:6]=[CH:7][N:8]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=1

참가 물질

6

반응물 3

HCID 70592633-Chloro-4-(3-fluorobenzyloxy)anilineHCID 10176127Pyridinium chlorideHCID 552958947-(methylthio)-1H-pyrazolo[4,3-d]pyrimidine

생성물 1

HCID 57597221N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-1H-pyrazolo[4,3-d]pyrimidin-7-amine수율 66%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

A mixture of 7-(methylthio)-1H-pyrazolo[4,3-d]pyrimidine (known compound from literature: J. Am. Chem. Soc., 1956, 78, 2418) (150 mg), 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (227 mg) and pyridine hydrochloride (156 mg) in 1-methyl-2-pyrrolidone (3 mL) was stirred at 120° C. for 10 hrs. After the completion of the reaction, the mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (hexane/ethyl acetate=1/3→1/10) to give the title compound (220 mg, yield 61%) as a pale-yellow solid.

후처리

  1. customAfter the completion of the reaction
  2. washwashed with saturated aqueous sodium hydrogen carbonate and saturated brine
  3. concentrationThe organic layer was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-83cb66cbe62e43e6931e15c7c12f4ff8
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178543B2

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