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Methyl morpholine oxide → N-(1-benzyl-1H-indazol-4-yl)-6-(1,2-dihydroxyethyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 706764
ノート
印刷プレビュー

反応式

HRID 706764 の反応式
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([NH:17][C:18]([C:20]3[N:24]4[CH:25]=C(C=C)[CH:27]=[CH:28][C:23]4=[N:22][CH:21]=3)=[O:19])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:35]CC1.[CH3:39][C:40]([CH3:42])=[O:41].O>C(O)(C)(C)C.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([NH:17][C:18]([C:20]3[N:24]4[CH:25]=[C:39]([CH:40]([OH:41])[CH2:42][OH:35])[CH:27]=[CH:28][C:23]4=[N:22][CH:21]=3)=[O:19])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 82029Methyl morpholine oxideHCID 18366337Propan-2-one--water (1/1)HCID 67975918N-(1-benzyl-1H-indazol-4-yl)-6-vinylimidazo[1,2-a]pyridine-3-carboxamide

生成物 1

HCID 67990296N-(1-benzyl-1H-indazol-4-yl)-6-(1,2-dihydroxyethyl)imidazo[1,2-a]pyridine-3-carboxamide

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒2 回
HCID 6386tert-Butanol溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of N-(1-benzyl-1H-indazol-4-yl)-6-vinylimidazo[1,2-a]pyridine-3-carboxamide (63 mg; 0.16 mmol), osmium tetroxide (0.008 mmol; 2.5% solution in t-butanol) and N-methylmorpholine N-oxide (21 mg; 0.18 mmol) in acetone/water (3:2; 1 mL) was stirred at ambient temperature for 24 hours. Additional osmium tetroxide was added (250 μL of a 2.5% solution in t-butanol) and the mixture was stirred for an additional 24 hours. The mixture was diluted with ethyl acetate and solids were isolated by filtration. The material was purified by reverse phase chromatography (acetonitrile/water) to give the desired product as a solid (3.6 mg). MS (APCI), m/z=428.2 (M+H).

後処理

  1. stirringwas stirred for an additional 24 hours
  2. customsolids were isolated by filtration
  3. customThe material was purified by reverse phase chromatography (acetonitrile/water)

出典と根拠

ORDレコード
ord-ad9e06af537744dab76e8097be96f854
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09174981B2

反応ノート

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