1H-Indazol-6-amine → 2-Chloro-N-(1H-indazol-6-yl)-5-methyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 645695노트

반응식

HRID 645695 반응식
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[N:7]=1.[NH2:23][C:24]1[CH:32]=[C:31]2[C:27]([CH:28]=[N:29][NH:30]2)=[CH:26][CH:25]=1.CCN(C(C)C)C(C)C>C(O)CCC.C(OC(=O)C)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:23][C:24]2[CH:32]=[C:31]3[C:27]([CH:28]=[N:29][NH:30]3)=[CH:26][CH:25]=2)[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[N:7]=1

참가 물질

6

반응물 3

HCID 814231H-Indazol-6-amineHCID 81531DiisopropylethylamineHCID 582908522,4-Dichloro-5-methyl-7-tosyl-7h-pyrrolo[2,3-d]pyrimidine

생성물 1

HCID 866280372-Chloro-N-(1H-indazol-6-yl)-5-methyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine수율 39.7%

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

To a solution of 2,4-dichloro-5-methyl-7-tosyl-pyrrolo[2,3-d]pyrimidine (0.36 g, 1 mmol) in n-butyl alcohol (3 mL) was added 6-aminoindazole (0.27 g, 2 mmol) and DIPEA (0.27 mL, 1.5 mmol) at room temperature. After heating at 90° C. for 4 h, the mixture was diluted with ethylacetate and the organic layer was sequentially washed with 1N HCl, saturated NaHCO3, and brine. The organic extract was then dried over Na2SO4 and concentrated to give a crude residue, which was purified by flash column (Hex/EtOAc=1:1) to give 2-Chloro-N-(1H-indazol-6-yl)-5-methyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.18 g).

후처리

  1. washthe organic layer was sequentially washed with 1N HCl, saturated NaHCO3, and brine
  2. extractionThe organic extract
  3. dry with materialwas then dried over Na2SO4
  4. concentrationconcentrated
  5. customto give a crude residue, which
  6. customwas purified by flash column (Hex/EtOAc=1:1)

출처 및 근거

ORD 기록
ord-05c1d9062c7f4ef0ab9e01e7fa29bed3
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705004B2

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