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

2,2-Dimethoxypropane → Cdc7-IN-15

HRID 2364072
ノート
印刷プレビュー

反応式

HRID 2364072 の反応式
[NH2:1][C:2]1[CH:6]=[C:5](Br)[S:4][C:3]=1[C:8]([NH2:10])=[O:9].CO[C:13](OC)([CH3:15])[CH3:14].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.[O-]S([O-])(=O)=O.[Mg+2].[CH3:39][C:40]1[C:44](B2OC(C)(C)C(C)(C)O2)=[CH:43][N:42](C(OC(C)(C)C)=O)[N:41]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.COCCOC.CC(N(C)C)=O>[CH3:14][C:13]1([CH3:15])[NH:1][C:2]2[CH:6]=[C:5]([C:44]3[CH:43]=[N:42][NH:41][C:40]=3[CH3:39])[S:4][C:3]=2[C:8](=[O:9])[NH:10]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

10

反応物 6

HCID 64952,2-DimethoxypropaneHCID 10340Sodium CarbonateHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 24083Sulfuric acid magnesium salt (1:1)HCID 219758623-Amino-5-bromothiophene-2-carboxamideHCID 53216815Tert-butyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrazole-1-carboxylate

生成物 1

HCID 66743505Cdc7-IN-15収率 86%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 3-amino-5-bromothiophene-2-carboxamide (1.99 g, 9.0 mmol), 2,2-dimethoxypropane (10 mL), CSA (209 mg, 0.90 mmol), MgSO4 (2.17 g, 18 mmol) and DMA (10 mL) was stirred at 90° C. for 2 h. After removal of MgSO4 by filtration, saturated aqueous NaHCO3 was added to the filtrate. The organic materials were extracted with EtOAc. The combined extracts were washed with water and brine, dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, a brown crystalline solid was obtained. A flask was charged with this solid, tert-butyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (6.0 g, 19.5 mmol), sodium carbonate (2.3 g, 38.3 mmol), 1,2-dimethoxyethane (30 mL) and water (15 mL). The flask was purged with argon. Then, 1,1′-bis(diphenylphosphino)ferrocenepalladium (II) dichloride dichloromethane adduct (626 mg, 0.766 mmol) was added to the mixture. The flask was purged with argon again. After stirring at 100° C. for 3.5 h, 8 M aqueous NaOH (2.0 mL) was added. After stirring at 100° C. for 1 h, the organic materials were extracted with EtOAc/THF. The combined extracts were dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, silica gel, EtOAc to 90:10 EtOAc/MeOH) to give the title compound (1.97 g, 86%) as a brown solid:

後処理

  1. customAfter removal of MgSO4
  2. filtrationby filtration, saturated aqueous NaHCO3
  3. additionwas added to the filtrate
  4. extractionThe organic materials were extracted with EtOAc
  5. washThe combined extracts were washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customAfter removal of the solvent at reduced pressure
  9. customa brown crystalline solid was obtained
  10. customThe flask was purged with argon
  11. customThe flask was purged with argon again
  12. stirringAfter stirring at 100° C. for 3.5 h
  13. addition8 M aqueous NaOH (2.0 mL) was added
  14. stirringAfter stirring at 100° C. for 1 h
  15. extractionthe organic materials were extracted with EtOAc/THF
  16. dry with materialThe combined extracts were dried over Na2SO4
  17. filtrationfiltered
  18. customAfter removal of the solvent at reduced pressure
  19. customthe residue was purified by column chromatography (Purif, silica gel, EtOAc to 90:10 EtOAc/MeOH)

出典と根拠

ORDレコード
ord-1b0d14fe1cef4c11a847ffbd1c845032
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08691828B2

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