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Triethylamine → (1,1-Dimethylethyl) [[4-[[2-[2-(aminocarbonyl)-4-[5,5-bis(4-fluorophenyl)pentyl]-1-piperazinyl]acetyl]amino]-3,5-dichlorophenyl]methyl]carbamate

HRID 1073183
ノート
印刷プレビュー

反応式

HRID 1073183 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][NH:16][CH:15]([C:19]([NH2:21])=[O:20])[CH2:14]2)=[CH:4][CH:3]=1.[Cl:29][C:30]1[CH:31]=[C:32]([CH2:42][NH:43][C:44](=[O:50])[O:45][C:46]([CH3:49])([CH3:48])[CH3:47])[CH:33]=[C:34]([Cl:41])[C:35]=1[NH:36][C:37](=[O:40])[CH2:38]Cl.C(N(CC)CC)C>CN(C)C=O>[NH2:21][C:19]([CH:15]1[CH2:14][N:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH:8]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:18][CH2:17][N:16]1[CH2:38][C:37]([NH:36][C:35]1[C:34]([Cl:41])=[CH:33][C:32]([CH2:42][NH:43][C:44](=[O:50])[O:45][C:46]([CH3:48])([CH3:47])[CH3:49])=[CH:31][C:30]=1[Cl:29])=[O:40])=[O:20]
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

5

反応物 3

HCID 8471TriethylamineHCID 147225494-[5,5-Bis(4-fluorophenyl)pentyl]-2-piperazinecarboxamideHCID 14722566(1,1-Dimethylethyl) [[3,5-dichloro-4-[(2-chloroacetyl)amino]phenyl)methyl)carbamate

生成物 1

HCID 14722567(1,1-Dimethylethyl) [[4-[[2-[2-(aminocarbonyl)-4-[5,5-bis(4-fluorophenyl)pentyl]-1-piperazinyl]acetyl]amino]-3,5-dichlorophenyl]methyl]carbamate収率 80.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A mixture of 7 parts of 4-[5,5-bis(4-fluorophenyl)pentyl]-2-piperazinecarboxamide, 6.6 parts of (1,1-dimethylethyl) [[3,5-dichloro-4-[(2-chloroacetyl)amino]phenyl)methyl)carbamate, 2.8 parts of N,N-diethylethanamine and 94 parts of N,N-dimethylformamide was stirred over weekend at 70° C. The reaction mixture was evaporated and the residue was taken up in water. 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, (96:4 by volume) as eluent. The desired fractions were collected and the eluent was evaporated, yielding 8.7 parts (80.7%) of (1,1-dimethylethyl) [[4-[[2-[2-(aminocarbonyl)-4-[5,5-bis(4-fluorophenyl)pentyl]-1-piperazinyl]acetyl]amino]-3,5-dichlorophenyl]methyl]carbamate as a residue (int. 102).

後処理

  1. customThe reaction mixture was evaporated
  2. extractionThe product was extracted twice with dichloromethane
  3. washThe combined extracts were washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol
  9. customThe desired fractions were collected
  10. customthe eluent was evaporated

出典と根拠

ORDレコード
ord-1c15dfe291d34cfc9fa08e30a30cd558
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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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