Pyridine → HCID 67063093、化合物

HRID 599338ノート

反応式

HRID 599338 の反応式
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.Cl[C:24]([O:26][C:27]([CH3:29])=[CH2:28])=[O:25]>C(Cl)Cl>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:24](=[O:25])[O:26][C:27]([CH3:29])=[CH2:28])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 1049PyridineHCID 93846Isopropenyl chloroformateHCID 7706343-tert-butyl-1-phenyl-1H-pyrazol-5-amine

生成物 1

HCID 67063093HCID 67063093、化合物収率 78%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
60 °C

実験手順

To a solution of Example B1 (10.00 g, 46.4 mmol, 1.00 eq) and pyridine (7.58 ml, 92.9 mmol, 2.00 eq) in CH2Cl2 (225 ml) at 0° C. was added isopropenyl chloroformate (5.33 ml, 4.8.8 mol, 1.05 eq). After 45 min at 0° C., the completed reaction was washed with 3M HCl (2×), satd. NaHCO3 (1×), and brine (1×), dried (MgSO4), filtered and evaporated to afford crude product (14.9 g) as an oil that solidified on the pump. The crude material obtained was upgraded by triturating in warm (60° C.) hexanes (70 ml) for 20-30 min until a powdery precipitate was obtained. After cooling to RT, the solids were collected by filtration, rinsing forward with hexanes. The cake was washed with more hexanes and then dried on the filter to afford prop-1-en-2-yl 3-t-butyl-1-phenyl-1H-pyrazol-5-ylcarbamate (10.79 g, 78% yield) as a tan powder which was used as is in the next reaction. MS (ESI) m/z: 300.3 (M+H+).

後処理

  1. customthe completed reaction
  2. washwas washed with 3M HCl (2×)
  3. dry with materialNaHCO3 (1×), and brine (1×), dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto afford crude product (14.9 g) as an oil that
  7. customThe crude material obtained
  8. customby triturating
  9. customwas obtained
  10. temperatureAfter cooling to RT
  11. filtrationthe solids were collected by filtration
  12. washrinsing forward with hexanes
  13. washThe cake was washed with more hexanes
  14. customdried on the
  15. filtrationfilter

出典と根拠

ORDレコード
ord-1d819bbe5efa4e69bd34496d4da6b945
出典データセット
uspto-grants-2011_03
特許番号
US07897762B2

反応ノート

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