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Hydrochloric Acid → 1-ethyl-3-methyl-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine hydrochloride

HRID 375849
ノート
印刷プレビュー

反応式

HRID 375849 の反応式
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]2[N:12]([CH2:16][CH3:17])[N:13]=[C:14]([CH3:15])[C:3]=12.[CH:18]1([CH2:24][NH2:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[NH4+].[OH-].Cl>C(Cl)Cl.O.CS(C)=O>[ClH:1].[CH2:16]([N:12]1[C:4]2=[N:5][C:6]3[C:11]([C:2]([NH:25][CH2:24][CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:3]2[C:14]([CH3:15])=[N:13]1)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH3:17]
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 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 76688CyclohexanemethylamineHCID 195922341-ethyl-3-methyl-4-chloro-1H-pyrazolo[3,4-b]quinoline

生成物 1

HCID 212177241-ethyl-3-methyl-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine hydrochloride

試薬・触媒・溶媒 3

HCID 679
Dimethyl Sulfoxide
溶媒
HCID 962Water溶媒
HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

A mixture of 4-chloro-1-ethyl-3-methyl-1H-pyrazolo[3,4-b]quinoline (1.0 g, 0.0043 mmol), cyclohexanemethylamine (1.2 ml, 0.009 mol) and DMSO (3 ml) was heated at 80° C. overnight. The reaction mixture was pured into water (100 ml)/NH4OH (0.5 ml) and was extracted with CH2Cl2. The solvent was evaporated to about 20 ml and then the mixture was purified by chromatography on silica gel, followed by high pressure liquid chromatography eluting with 20% EtOAc/hexane to 50% EtOAc/hexane to afford the product as the free base. The free base was dissolved in CH2Cl2 (20 ml) and treated with ethereal HCl and the solution was evaporated. The residue was crystallized from ethyl acetate/ether/ethanol to afford 1-ethyl-3-methyl-N-(cyclohexylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine hydrochloride, m.p. 215°-217° C.

後処理

  1. extractionwas extracted with CH2Cl2
  2. customThe solvent was evaporated to about 20 ml
  3. customthe mixture was purified by chromatography on silica gel
  4. washeluting with 20% EtOAc/hexane to 50% EtOAc/hexane
  5. customto afford the product as the free base
  6. customthe solution was evaporated
  7. customThe residue was crystallized from ethyl acetate/ether/ethanol

出典と根拠

ORDレコード
ord-fe67965e050e43a6b0878baca7d229e6
出典データセット
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05488055

反応ノート

読み込み中…

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