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Methyl triflate → (S)-10-{3-[2-(4-Fluoro-phenyl)-ethyl]-piperazin-1-yl}-2-isopropyl-4H-3-thia-1,4,9-triaza-benzo[f]azulene

HRID 1350462
ノート
印刷プレビュー

反応式

HRID 1350462 の反応式
[CH:1]([C:4]1[S:13][C:12]2[NH:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[NH:8][C:7](=S)[C:6]=2[N:5]=1)([CH3:3])[CH3:2].FC(F)(F)S([O:24][CH3:25])(=O)=O.[F:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][C@H:37]2[CH2:42][NH:41][CH2:40][CH2:39][NH:38]2)=[CH:31][CH:30]=1>ClCCl.N1C=CC=CC=1>[NH3:5].[CH3:25][OH:24].[F:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][C@@H:37]2[NH:38][CH2:39][CH2:40][N:41]([C:7]3[C:6]4[N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[S:13][C:12]=4[NH:11][C:10]4[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=4[N:8]=3)[CH2:42]2)=[CH:31][CH:30]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 9526Methyl triflateHCID 210934792-Isopropyl-4,9-dihydro-3-thia-1,4,9-triazabenzo[f]azulene-10-thioneHCID 69487151(S)-2-(2-(4-Fluoro-phenyl)-ethyl)-piperazine

生成物 2

HCID 21705897Ammonia methanolHCID 136005614(S)-10-{3-[2-(4-Fluoro-phenyl)-ethyl]-piperazin-1-yl}-2-isopropyl-4H-3-thia-1,4,9-triaza-benzo[f]azulene収率 78.7%

試薬・触媒・溶媒

2
HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

実験手順

Stir 2-isopropyl-4,9-dihydro-3-thia-1,4,9-triaza-benzo[f]azulene-10-thione (0.551 g, 2.0 mmol) in dichloromethane (10.0 mL) and chilled in an ice bath while adding methyl trifluoromethane sulfonate (0.27 mL, 2.4 mmol). Allow this solution to stir at ambient temperature for 16 hours. Evaporate the solvent to a gray solid. Dissolve this solid and (S)-2-[2-(4-fluoro-phenyl)-ethyl]-piperazine (0.417 g, 2.0 mmol) in pyridine (8.0 mL) and heat at 115° C. for 23 hours. After evaporation of the pyridine, silica gel chromatography, eluting with methylene chloride: 2N NH3/methanol (100:5), gives 0.354 g of the title compound as a yellow solid: mass spectrum (ion spray): m/z=450 (M+1); Analysis for C25H28FN5S(0.2 H2O): calcd: C, 66.26; H, 6.32; N, 15.45; found: C, 66.01; H, 6.15; N, 15.25.

後処理

  1. temperaturechilled in an ice bath
  2. customEvaporate the solvent to a gray solid
  3. temperatureheat at 115° C. for 23 hours
  4. customAfter evaporation of the pyridine, silica gel chromatography
  5. washeluting with methylene chloride

出典と根拠

ORDレコード
ord-4ae1470cffe742eea7750ceda4dc7fd8
出典データセット
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07214673B2

反応ノート

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