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

Hydrochloric Acid → (+/-)-2-(1-Amino-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethyl)benzo[d]oxazole-5-carbonitrile

HRID 2174087
ノート
印刷プレビュー

反応式

HRID 2174087 の反応式
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([C:20]3[C:28]([O:29][CH3:30])=[CH:27][C:26]([CH3:31])=[C:25]4[C:21]=3[CH:22]=[CH:23][N:24]4C(OC(C)(C)C)=O)([NH:13]S(C(C)(C)C)=O)[CH3:12])=[N:8][C:7]=2[CH:39]=1)#[N:2].Cl>O1CCOCC1>[NH2:13][C:11]([C:9]1[O:10][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:39][C:7]=2[N:8]=1)([C:20]1[C:28]([O:29][CH3:30])=[CH:27][C:26]([CH3:31])=[C:25]2[C:21]=1[CH:22]=[CH:23][NH:24]2)[CH3:12]
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

4

反応物 2

HCID 313Hydrochloric AcidHCID 86701723tert-butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-(1,1-dimethylethylsulfinamido)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

生成物 1

HCID 86701722(+/-)-2-(1-Amino-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethyl)benzo[d]oxazole-5-carbonitrile

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
60 °C

実験手順

To a solution of tert-butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-(1,1-dimethylethylsulfinamido)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (120 mg, 0.218 mmol) in dioxane (1 mL) was added 4M HCl in dioxane (2.2 mL, 8.72 mmol) and the mixture was stirred at 60° C. After 2 hours the reaction was cooled in an ice bath and quenched with 30% aq. NH4OH (2.18 mL). Water was added, the layers were separated and the aqueous layer was extracted with EtOAc, dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-100% EtOAc:Heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.92 (br. s., 1H) 8.29 (dd, J=1.39, 0.88 Hz, 1H) 7.72-7.85 (m, 2H) 7.28 (t, J=2.84 Hz, 1H) 7.05-7.16 (m, 1H) 6.64 (s, 1H) 3.19 (s, 3H) 2.59 (br. s., 2H) 2.43 (s, 3H) 1.90 (s, 3H). HRMS calcd. for C20H18N4O2 (M+H)+ 347.1503. found 347.1486.

後処理

  1. temperatureAfter 2 hours the reaction was cooled in an ice bath
  2. customquenched with 30% aq. NH4OH (2.18 mL)
  3. additionWater was added
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by flash chromatography (0-100% EtOAc:Heptanes)

出典と根拠

ORDレコード
ord-d480424db5674bf0b7c23d6c4b41c172
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09056874B2

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