Sodium ethoxide → HCID 178440265、化合物

HRID 1860572ノート

反応式

HRID 1860572 の反応式
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=2[Cl:15])[N:5]=[C:4]([CH:16]([CH3:18])[CH3:17])[C:3]=1[C:19]([NH2:21])=[O:20].[NH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([CH2:32][C:33](OCC)=O)[CH:30]=2)[NH:25][N:24]=1.[O-]CC.[Na+]>C(O)C>[Cl:13][C:12]1[CH:11]=[C:10]([Cl:14])[CH:9]=[C:8]([Cl:15])[C:7]=1[N:6]1[C:2]2=[N:1][C:33]([CH2:32][C:29]3[CH:30]=[C:31]4[C:26](=[CH:27][CH:28]=3)[NH:25][N:24]=[C:23]4[NH2:22])=[N:21][C:19](=[O:20])[C:3]2=[C:4]([CH:16]([CH3:18])[CH3:17])[NH:5]1

参加物

5

反応物 3

HCID 2723922Sodium ethoxideHCID 185406305-Amino-3-isopropyl-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamideHCID 18540672Ethyl 3-aminoindazol-5-ylacetate

生成物 1

HCID 178440265HCID 178440265、化合物

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

To a stirred solution of 139 mg (0.40 mmol) of 5-amino-3-isopropyl-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamide in 3 mL of absolute ethanol was added 329 mg (1.50 mmol) of ethyl 3-aminoindazol-5-ylacetate followed by 1.13 mL (3.0 mmol) of 2.66 M sodium ethoxide in ethanol. The solution was stirred 16 h at reflux, and the heating mantle was then removed. The reaction was treated with 8 mL of 10% aq. HOAc, poured into water, and extracted with EtOAc. The organic extract was washed with brine, dried (MgSO4), concentrated under reduced pressure, and chromatographed on silica gel (gradient elution with 5% to 10% MeOH—CH2Cl2) to give, after removal of solvent, 123 mg (61%) of 1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(3-aminoindazol-5-ylmethyl)pyrazolo[3,4-d]pyrimidin-4-one as a white, amorphous solid. Mass spec.: 502.0712 (M+H)+.

後処理

  1. temperatureat reflux
  2. customthe heating mantle was then removed
  3. additionThe reaction was treated with 8 mL of 10% aq. HOAc
  4. additionpoured into water
  5. extractionextracted with EtOAc
  6. extractionThe organic extract
  7. washwas washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated under reduced pressure
  10. customchromatographed on silica gel (gradient elution with 5% to 10% MeOH—CH2Cl2)
  11. customto give
  12. customafter removal of solvent, 123 mg (61%) of 1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(3-aminoindazol-5-ylmethyl)pyrazolo[3,4-d]pyrimidin-4-one as a white, amorphous solid

出典と根拠

ORDレコード
ord-b0e726281b794c7d91327139985e7fc5
出典データセット
uspto-grants-2003_03
特許番号
US06531477B1

反応ノート

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