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1H-Indazole → (4-Chloro-phenyl)-(2-indazol-2-yl-6-methyl-pyrimidin-4-yl)-amine

HRID 1514349
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HRID 1514349 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:5]=[C:4]([CH3:16])[N:3]=1.[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[N:18]1>C(#N)C>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6]2[CH:5]=[C:4]([CH3:16])[N:3]=[C:2]([N:18]3[CH:19]=[C:20]4[C:25]([CH:24]=[CH:23][CH:22]=[CH:21]4)=[N:17]3)[N:7]=2)=[CH:10][CH:11]=1.[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6]2[CH:5]=[C:4]([CH3:16])[N:3]=[C:2]([N:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=[N:18]3)[N:7]=2)=[CH:10][CH:11]=1
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참가 물질

5

반응물 2

HCID 92211H-IndazoleHCID 58026187(2-Chloro-6-methyl-pyrimidin-4-yl)-(4-chloro-phenyl)-amine

생성물 2

HCID 24764453(4-Chloro-phenyl)-(2-indazol-2-yl-6-methyl-pyrimidin-4-yl)-amine수율 14%HCID 24825861(4-Chloro-phenyl)-(2-indazol-1-yl-6-methyl-pyrimidin-4-yl)-amine수율 5.3%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

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온도
160 °C

실험 절차

(2-Chloro-6-methyl-pyrimidin-4-yl)-(4-chloro-phenyl)-amine (300 mg, 1.18 mmol) was dissolved in acetonitrile (4 mL), indazole (150 mg, 1.3 mmol) was added and the mixture was heated in a microwave oven at 160° C. for 30 minutes. The solvent was removed in vacuo and the remaining residue was basified with aqueous sodium hydrogencarbonate and extracted with chloroform. The combined organic phases were dried with sodium sulphate, filtrated and evaporated. The crude product was purified by column chromatography with ethyl acetate-hexane as eluent to give (4-chloro-phenyl)-(2-indazol-2-yl-6-methyl-pyrimidin-4-yl)-amine (56 mg, 14%, mp=224.7-226.7° C.) (LC-ESI-HRMS of [M+H]+ shows 336.1019 Da. Calc. 336.101598 Da, dev. 0.9 ppm) as a white solid and (4-chloro-phenyl)-(2-indazol-1-yl-6-methyl-pyrimidin-4-yl)-amine (21 mg, 5.3%, mp=166.7-168.7° C.) (LC-ESI-HRMS of [M+H]+ shows 336.1007 Da. Calc. 336.101598 Da, dev. −2.7 ppm) as a white solid.

후처리

  1. customThe solvent was removed in vacuo
  2. extractionextracted with chloroform
  3. dry with materialThe combined organic phases were dried with sodium sulphate
  4. filtrationfiltrated
  5. customevaporated
  6. customThe crude product was purified by column chromatography with ethyl acetate-hexane as eluent

출처 및 근거

ORD 기록
ord-31488919fec946ebb872a34974a54076
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08222262B2

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