ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecane → 4-(4-Methyl-2-(2-propylthiazolo[5,4-b]pyridin-7-ylamino)phenylthio)phenol

HRID 607148
ノート
印刷プレビュー

反応式

HRID 607148 の反応式
C(N1CCN2CCN(CC(C)C)P1N(CC(C)C)CC2)C(C)C.CC(C)([O-])C.[Na+].Cl[C:31]1[CH:36]=[CH:35][N:34]=[C:33]2[S:37][C:38]([CH2:40][CH2:41][CH3:42])=[N:39][C:32]=12.[NH2:43][C:44]1[CH:49]=[C:48]([CH3:50])[CH:47]=[CH:46][C:45]=1[S:51][C:52]1[CH:57]=[CH:56][C:55]([OH:58])=[CH:54][CH:53]=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:50][C:48]1[CH:47]=[CH:46][C:45]([S:51][C:52]2[CH:57]=[CH:56][C:55]([OH:58])=[CH:54][CH:53]=2)=[C:44]([NH:43][C:31]2[CH:36]=[CH:35][N:34]=[C:33]3[S:37][C:38]([CH2:40][CH2:41][CH3:42])=[N:39][C:32]=23)[CH:49]=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 4

HCID 45712432,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecane2 回HCID 23676156Sodium t-butoxideHCID 668081234-(2-Amino-4-methyl-phenylsulfanyl)-phenolHCID 668084877-Chloro-2-propyl-thiazolo[5,4-b]pyridine

生成物 1

HCID 250106684-(4-Methyl-2-(2-propylthiazolo[5,4-b]pyridin-7-ylamino)phenylthio)phenol収率 8.3%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒2 回HCID 1140Toluene溶媒

実験手順

A dry nitrogen-purged flask was charged with 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phospha-bicyclo[3.3.3]undecane (40.4 mg, 0.118 mmol), tris(dibenzylideneacetone)-dipalladium (27 mg, 0.0295 mmol), and sodium tert-butoxide (87.7 mg, 0.885 mmol). A solution of the product of Example 5G (125.5 mg, 0.590 mmol) in anhydrous toluene (5 mL) was added via syringe, followed by the product from Example 6c (136 mg, 0.590 mmol). The reaction was heated at reflux in a preheated 110° oil bath for 14 hours, cooled to room temperature, treated with additional 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phospha-bicyclo[3.3.3]undecane (40.4 mg) and tris(dibenzylideneacetone)dipalladium (27 mg), and heated at reflux for an additional 7 hours. The reaction was cooled to room temperature and the solvent removed by rotary evaporation in vacuo. Purification by silica gel flash chromatography with a gradient of 15% to 30% ethyl acetate/methylene chloride gave impure material. Purification by silica gel flash chromatography with a gradient of 1% to 2% methanol/methylene chloride afforded the desired title compound as a light yellow solid (20 mg, 0.049 mmol, 8%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.03 (t, J=7.35 Hz, 3H) 1.76-1.94 (m, 2H) 2.31 (s, 3H) 3.10 (t, J=7.35 Hz, 2H) 5.76 (s, 1H) 6.67-6.73 (m, 2H) 6.96-7.04 (m, 1H) 7.08-7.14 (m, 1H) 7.20 (d, J=8.46 Hz, 2H) 7.29 (s, 1H) 8.14 (d, J=5.52 Hz, 1H) 8.55 (s, 1H) 9.73 (s, 1H); MS (DCI/NH3) m/z 408 (M+H)+.

後処理

  1. customA dry nitrogen-purged flask
  2. temperatureThe reaction was heated
  3. temperatureat reflux in a preheated 110° oil bath for 14 hours
  4. temperatureheated
  5. temperatureat reflux for an additional 7 hours
  6. temperatureThe reaction was cooled to room temperature
  7. customthe solvent removed by rotary evaporation in vacuo
  8. customPurification by silica gel flash chromatography with a gradient of 15% to 30% ethyl acetate/methylene chloride
  9. customgave impure material
  10. customPurification by silica gel flash chromatography with a gradient of 1% to 2% methanol/methylene chloride

出典と根拠

ORDレコード
ord-6751c4f4919640af8d19829422dd6ad5
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07915411B2

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