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Thiophene → HCID 86619164、化合物

HRID 1530931
ノート
印刷プレビュー

反応式

HRID 1530931 の反応式
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH:9]1[CH2:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([F:26])[CH:17]=1)=[O:7].[CH3:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([CH3:43])[C:38]=1[NH:44][C:45](=[O:53])[CH2:46][N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1.S1C=CC=C1>CC(O)C.[Pt].CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[F:32][C:30]([F:31])([F:33])[C:28]1[CH:27]=[C:5]([CH:4]=[C:3]([C:2]([F:35])([F:1])[F:34])[CH:29]=1)[C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([N:50]2[CH2:51][CH2:52][N:47]([CH2:46][C:45]([NH:44][C:38]3[C:39]([CH3:43])=[CH:40][CH:41]=[CH:42][C:37]=3[CH3:36])=[O:53])[CH2:48][CH2:49]2)[CH2:10][C@@H:9]1[CH2:15][C:16]1[CH:21]=[C:20]([C:22]([F:24])([F:23])[F:25])[CH:19]=[C:18]([F:26])[CH:17]=1)=[O:7].[F:32][C:30]([F:31])([F:33])[C:28]1[CH:27]=[C:5]([CH:4]=[C:3]([C:2]([F:35])([F:1])[F:34])[CH:29]=1)[C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([N:50]2[CH2:51][CH2:52][N:47]([CH2:46][C:45]([NH:44][C:38]3[C:39]([CH3:43])=[CH:40][CH:41]=[CH:42][C:37]=3[CH3:36])=[O:53])[CH2:48][CH2:49]2)[CH2:10][C@@H:9]1[CH2:15][C:16]1[CH:21]=[C:20]([C:22]([F:24])([F:23])[F:25])[CH:19]=[C:18]([F:26])[CH:17]=1)=[O:7]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 8030ThiopheneHCID 2608606Cvt-2738HCID 18630841HCID 18630841、化合物

生成物 2

HCID 86619163HCID 86619163、化合物収率 10%HCID 86619164HCID 86619164、化合物収率 12%

試薬・触媒・溶媒 3

HCID 11026
Titanium isopropoxide
触媒
HCID 23939Platinum触媒
HCID 3776Isopropanol溶媒

実験手順

A mixture of (±)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-[[3-fluoro-5-(trifluoromethyl)phenyl]methy]-4-piperidinone (0.01 mol) and N-(2,6-dimethylpheny)-1-piperazine-acetamide (0.01 mol) in 2-propanol (150 ml) was hydrogenated at 50° C. with platinum on activated carbon (55), 2 g) as a catalyst in the presence of titanium(IV)isopropoxide (2.84 g) and thiophene solution (1 ml). After uptake of hyrogen, the catalyst was filtered off and the filtrate was evaporated. The residue was taken up in CH2Cl2 and H2O. The organic layer was separated, washed several times with H2O, dried, filtered over dicalite and the solvent was evaporated. This fraction was purified by HPLC over silica gel (eluent: CH2Cl2/CH3OH 98/2). Two pure factions were collected and their solvents were evaporated. The residue was dried, yielding 0.72 g (10%) of (±)-cis-4-[1-[3,5-bis(trifluoromethyl)benzoyl]-2-[[3fluoro-5-(trifluoromethyl)phenyl]methyl]-4-piperidinyl]-N_(2,6-dimethylphenyl)-1-piperazineacetamide (compound 140 ) and 0.88 g (12%) of (±)-trans-4-[1-[3,5-bis(trifluoromethyl)benzoyl]-2-[[3-fluoro-5-(trifluoro-methyl)phenyl]methyl]-4-piperidinyl]-N_(2,6-dimethylphenyl)-1-piperazineacetamide (compound 141).

後処理

  1. filtrationAfter uptake of hyrogen, the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe organic layer was separated
  4. washwashed several times with H2O
  5. customdried
  6. filtrationfiltered over dicalite
  7. customthe solvent was evaporated
  8. customThis fraction was purified by HPLC over silica gel (eluent: CH2Cl2/CH3OH 98/2)
  9. customTwo pure factions were collected
  10. customtheir solvents were evaporated
  11. customThe residue was dried

出典と根拠

ORDレコード
ord-56f3861925414dbbbb28dd2fc38b3ed9
出典データセット
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06197772B1

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート