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Sodium Iodide → Formic acid 6-(4-morpholinylmethyl)-N-[6-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide

HRID 1616054
ノート
印刷プレビュー

反応式

HRID 1616054 の反応式
Cl[CH2:2][C:3]1[N:8]=[C:7]([C:9]([NH:11][C:12]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]4[NH:27][CH:28]=[CH:29][C:22]=34)[CH:18]=[C:17]3[C:13]=2[CH:14]=[N:15][N:16]3S(C2C=CC=CC=2)(=O)=O)=[O:10])[CH:6]=[CH:5][CH:4]=1.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.CCN(C(C)C)C(C)C.[I-].[Na+].C[Si](C)(C)[O-].[K+]>CC#N.C1COCC1>[CH:9]([OH:10])=[O:42].[N:39]1([CH2:2][C:3]2[N:8]=[C:7]([C:9]([NH:11][C:12]3[CH:20]=[C:19]([C:21]4[CH:26]=[CH:25][N:24]=[C:23]5[NH:27][CH:28]=[CH:29][C:22]=45)[CH:18]=[C:17]4[C:13]=3[CH:14]=[N:15][NH:16]4)=[O:10])[CH:6]=[CH:5][CH:4]=2)[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1
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

8

反応物 5

HCID 5238Sodium IodideHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 23668039Potassium trimethylsilanolateHCID 582679856-(Chloromethyl)-N-[1-(phenylsulfonyl)-6-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide

生成物 1

HCID 67158677
Formic acid 6-(4-morpholinylmethyl)-N-[6-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide
収率 62.3%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

6-(Chloromethyl)-N-[1-(phenylsulfonyl)-6-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide (0.05 g, 0.09 mmol) was dissolved in MeCN (0.5 ml) and added to a vessel containing morpholine (0.1 mmol). DIPEA (0.026 ml, 0.15 mmol) and sodium iodide (0.015 g, 0.1 mmol) were then added and the mixture was heated to 70° C. for 18 hr. Potassium trimethylsilanolate (0.5 mmol, 0.063 g), dissolved in THF (0.25 ml) was then added and the mixture was heated at 50° C. for 24 hrs. After cooling the solution was quenched with aqueous MeCN (50:50, 1 ml) and neutralised. Solvent was removed in a blowdown unit. The sample was then dissolved in DMF (200 μl), Acetone (200 μl) and water (20 μl) and purified by Mass Directed AutoPrep HPLC (Method F). The solvent was removed in vacuo using the Genevac to give the title compound (14 mg).

後処理

  1. additionadded to a vessel
  2. additionwas then added
  3. temperaturethe mixture was heated at 50° C. for 24 hrs
  4. temperatureAfter cooling the solution
  5. customwas quenched with aqueous MeCN (50:50, 1 ml)
  6. customSolvent was removed in a blowdown unit
  7. dissolutionThe sample was then dissolved in DMF (200 μl)
  8. customAcetone (200 μl) and water (20 μl) and purified by Mass Directed AutoPrep HPLC (Method F)
  9. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-4dd0c5f722bf44c0853fa18c05d3cca4
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08765743B2

反応ノート

読み込み中…

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