Dimethylformamide → 1-methyl-8-(methylthio)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 44580ノート

反応式

HRID 44580 の反応式
[CH3:1][N:2]1[C:14]2[C:13]3[N:12]=[C:11]([S:15][CH3:16])[N:10]=[CH:9][C:8]=3[CH2:7][CH2:6][C:5]=2[C:4]([C:17]([O:19]CC)=O)=[N:3]1.C[N:23](C)C=O.O.[NH4+]>CO>[CH3:1][N:2]1[C:14]2[C:13]3[N:12]=[C:11]([S:15][CH3:16])[N:10]=[CH:9][C:8]=3[CH2:7][CH2:6][C:5]=2[C:4]([C:17]([NH2:23])=[O:19])=[N:3]1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 22024077Azanium;hydrateHCID 45141606Ethyl 1-methyl-8-(methylthio)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

生成物 1

HCID 451416071-methyl-8-(methylthio)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide収率 52%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
65 °C

実験手順

13.00 g (0.043 mol) of ethyl 1-methyl-8-(methylthio)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate were suspended in a mixture of 200 mL of methanol, 200 mL of dimethylformamide and 200 mL of ammonium hydrate 30%. The mixture was stirred at 65° C. in a closed bottle for about 8 hours. The solvent was then evaporated to dryness, the residue redissolved with dichloromethane and washed with water. The organic layer was dried over Na2SO4 and evaporated. The crude was purified by chromatography on a silica gel column eluted by a mixture cyclohexane/ethyl acetate, giving 6.16 g (52% yield) of the title compound.

後処理

  1. customThe solvent was then evaporated to dryness
  2. dissolutionthe residue redissolved with dichloromethane
  3. washwashed with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated
  6. customThe crude was purified by chromatography on a silica gel column
  7. washeluted by a mixture cyclohexane/ethyl acetate

出典と根拠

ORDレコード
ord-9280bad6438c4dc69322747c096c17b0
出典データセット
uspto-grants-2013_09
特許番号
US08541429B2

反応ノート

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