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

Dimethyl Sulfoxide → HCID 178516972、化合物

HRID 707449
ノート
印刷プレビュー

反応式

HRID 707449 の反応式
Cl.[NH2:2][C@H:3]1[CH2:6][C@H:5]([N:7]2[C:11]3=[N:12][CH:13]=[C:14]([Br:16])[N:15]=[C:10]3[N:9]([CH:17]3[CH2:19][CH2:18]3)[C:8]2=[O:20])[CH2:4]1.Cl[C:22]1[N:31]=[CH:30][C:29]2[C:24](=[CH:25][C:26]([F:32])=[CH:27][CH:28]=2)[N:23]=1.CS(C)=O.C(N(CC)C(C)C)(C)C>O.Cl.O1CCOCC1>[Br:16][C:14]1[N:15]=[C:10]2[N:9]([CH:17]3[CH2:18][CH2:19]3)[C:8](=[O:20])[N:7]([C@H:5]3[CH2:6][C@H:3]([NH:2][C:22]4[N:31]=[CH:30][C:29]5[C:24](=[CH:25][C:26]([F:32])=[CH:27][CH:28]=5)[N:23]=4)[CH2:4]3)[C:11]2=[N:12][CH:13]=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 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 210739782-Chloro-7-fluoroquinazolineHCID 178479283HCID 178479283、化合物2 回

生成物 1

HCID 178516972HCID 178516972、化合物収率 27%

試薬・触媒・溶媒 3

HCID 313
Hydrochloric Acid
溶媒
HCID 962Water溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A glass microwave reaction vessel was charged with 1-(trans-3-aminocyclobutyl)-5-bromo-3-cyclopropyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one hydrochloride (Intermediate 82, 0.143 g, 0.397 mmol) and 2-chloro-7-fluoroquinazoline (0.118 g, 0.646 mmol). DMSO (2 mL) was added followed by N,N-diisopropylethylamine (0.300 mL, 1.725 mmol) and the reaction mixture was sealed under argon and heated at 100° C. overnight. The reaction was cooled room temperature and diluted with water. The precipitate was filtered to give an off-white solid. The material was dissolved in 4M HCl in dioxane and purified by reverse-phase HPLC (Gilson; Gemini-NX 10 m C18 110A AXIA, 100×50 mm column) eluting with 0.1% TFA-H2O:0.1% TFA CH3CN (9:1→1:9). The fractions containing the desired product were combined and concentrated in vacuo. The residue was dissolved in MeOH and loaded onto an Si-Carbonate (Silicycle) cartridge eluting with DCM/MeOH to give 50 mg (27%) of a white crystalline solid. ESI MS 469.9, 471.8 [M+1].

後処理

  1. customA glass microwave reaction vessel
  2. customthe reaction mixture was sealed under argon
  3. temperatureThe reaction was cooled room temperature
  4. filtrationThe precipitate was filtered
  5. customto give an off-white solid
  6. custompurified by reverse-phase HPLC (Gilson; Gemini-NX 10 m C18 110A AXIA, 100×50 mm column)
  7. washeluting with 0.1% TFA-H2O
  8. additionThe fractions containing the desired product
  9. concentrationconcentrated in vacuo
  10. dissolutionThe residue was dissolved in MeOH
  11. washeluting with DCM/MeOH

出典と根拠

ORDレコード
ord-72129a68a69f4e57ba81603c9736c3b3
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09174992B2

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