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Dimethylformamide → Pirodavir

HRID 981645
ノート
印刷プレビュー

反応式

HRID 981645 の反応式
Cl[C:2]1[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.C(O)(=O)CCC(O)=O.[NH:17]1[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][O:25][C:26]2[CH:36]=[CH:35][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][CH:27]=2)[CH2:19][CH2:18]1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>ClCCl.O>[CH3:8][C:5]1[N:4]=[N:3][C:2]([N:17]2[CH2:18][CH2:19][CH:20]([CH2:23][CH2:24][O:25][C:26]3[CH:27]=[CH:28][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:35][CH:36]=3)[CH2:21][CH2:22]2)=[CH:7][CH:6]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 2272543-Chloro-6-methylpyridazineHCID 23056112Ethyl 4-[2-(4-piperidinyl)ethoxy]benzoate butanedioate

生成物 1

HCID 71345Pirodavir収率 56.8%

試薬・触媒・溶媒 2

HCID 962Water
溶媒
HCID 6344Dichloromethane溶媒

反応条件

温度
150 °C

実験手順

A mixture of 10.4 parts of 3-chloro-6-methylpyridazine, 22.4 parts of ethyl 4-[2-(4-piperidinyl)ethoxy]benzoate butanedioate (1:1), 8.6 parts of sodium carbonate and 0.9 parts of N,N-dimethylformamide was stirred for 3 hours in an oil bath at ±150° C. After cooling, water and dichloromethane were added and the layers were separated. The organic layer was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and ethanol (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2,2'-oxybispropane and 2-propanone (75:25 by volume). The precipitated product was filtered off and dried, yielding 17 parts (56.8%) of ethyl 4-[2-[1-(6-methyl-3-pyridazinyl)-4-piperidinyl]-ethoxy]benzoate; mp. 130.1° C. (comp. 1).

後処理

  1. temperatureAfter cooling
  2. customthe layers were separated
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and ethanol (99:1 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from a mixture of 2,2'-oxybispropane and 2-propanone (75:25 by volume)
  11. filtrationThe precipitated product was filtered off
  12. customdried

出典と根拠

ORDレコード
ord-c0bb6e8ba3744482b41dc34a03e9acfa
出典データセット
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04992433

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート