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Hydrochloric Acid → 2-(aminocarbonyl)-N-(4-(aminomethyl)-2,6-dichlorophenyl]-4-[5,5-bis(4-fluorophenyl)pentyl]-1-piperazineacetamide

HRID 1073193
ノート
印刷プレビュー

反応式

HRID 1073193 の反応式
[NH2:1][C:2]([CH:4]1[CH2:9][N:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:7][CH2:6][N:5]1[CH2:29][C:30]([NH:32][C:33]1[C:38]([Cl:39])=[CH:37][C:36]([CH2:40][NH:41]C(=O)OC(C)(C)C)=[CH:35][C:34]=1[Cl:49])=[O:31])=[O:3].CO.Cl>CC(O)C>[NH2:1][C:2]([CH:4]1[CH2:9][N:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[CH2:7][CH2:6][N:5]1[CH2:29][C:30]([NH:32][C:33]1[C:38]([Cl:39])=[CH:37][C:36]([CH2:40][NH2:41])=[CH:35][C:34]=1[Cl:49])=[O:31])=[O:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14722567(1,1-Dimethylethyl) [[4-[[2-[2-(aminocarbonyl)-4-[5,5-bis(4-fluorophenyl)pentyl]-1-piperazinyl]acetyl]amino]-3,5-dichlorophenyl]methyl]carbamate

生成物 1

HCID 147226602-(aminocarbonyl)-N-(4-(aminomethyl)-2,6-dichlorophenyl]-4-[5,5-bis(4-fluorophenyl)pentyl]-1-piperazineacetamide収率 44.9%

試薬・触媒・溶媒 1

HCID 3776
Isopropanol
溶媒

実験手順

A mixture of 8.7 parts of (1,1-dimethylethyl) [[4-[[2-[2-(aminocarbonyl)-4-[5,5-bis(4-fluorophenyl)pentyl]-1-piperazinyl]acetyl]amino]-3,5-dichlorophenyl]methyl]carbamate, 120 parts of methanol and 24 parts of 2-propanol, saturated with hydrogen chloride was stirred for 30 minutes at reflux temperature. The reaction mixture was evaporated and the residue was taken up in water. The whole was treated with an ammonium hydroxide solution and the product was extracted twice with dichloromethane. The combined extracts were washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (93:7 by volume) as eluent. The desired fraction was collected and the eluent was evaporated. The residue was suspended in 2,2'-oxybispropane. The product was filtered off and dried, yielding 3.34 parts (44.9%) of 2-(aminocarbonyl)-N-(4-(aminomethyl)-2,6-dichlorophenyl]-4-[5,5-bis(4-fluorophenyl)pentyl]-1-piperazineacetamide; mp. 160.8° C. (compound 100 ).

後処理

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. additionThe whole was treated with an ammonium hydroxide solution
  4. extractionthe product was extracted twice with dichloromethane
  5. washThe combined extracts were washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol
  11. customThe desired fraction was collected
  12. customthe eluent was evaporated
  13. filtrationThe product was filtered off
  14. customdried

出典と根拠

ORDレコード
ord-99e254bfaeae4faebc1c293037d6200e
出典データセット
uspto-grants-1990_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04968684

反応ノート

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