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Dimethyl Sulfoxide → [5-({[1-(4-Chloromethyl-benzyl)-1H-pyrazole-4-carbonyl]-amino}-methyl)-4,6-dimethyl-pyridin-2-yl]-carbamic acid tert-butyl ester

HRID 928395
ノート
印刷プレビュー

反応式

HRID 928395 の反応式
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([CH2:15][NH:16][C:17]([C:19]2[CH:20]=[N:21][N:22]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([CH2:31]O)=[CH:27][CH:26]=3)[CH:23]=2)=[O:18])=[C:10]([CH3:33])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C[Si]([Cl:39])(C)C.CS(C)=O.C([O-])(O)=O.[Na+]>>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([CH2:15][NH:16][C:17]([C:19]2[CH:20]=[N:21][N:22]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([CH2:31][Cl:39])=[CH:27][CH:26]=3)[CH:23]=2)=[O:18])=[C:10]([CH3:33])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

HCID 679Dimethyl SulfoxideHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 58081225[5-({[1-(4-Hydroxymethyl-benzyl)-1H-pyrazole-4-carbonyl]-amino}-methyl)-4,6-dimethyl-pyridin-2-yl]-carbamic acid tert-butyl ester

生成物 1

HCID 58081307[5-({[1-(4-Chloromethyl-benzyl)-1H-pyrazole-4-carbonyl]-amino}-methyl)-4,6-dimethyl-pyridin-2-yl]-carbamic acid tert-butyl ester

実験手順

A mixture of [5-({[1-(4-Hydroxymethyl-benzyl)-1H-pyrazole-4-carbonyl]-amino}-methyl)-4,6-dimethyl-pyridin-2-yl]-carbamic acid tert-butyl ester (100 mg, 0.2 mmol, for preparation see step D, example 16), trimethylsilyl chloride (47 mg, 0.4 mmol) and DMSO (4 mg, 0.06 mmol) was stirred at RT for 10 min. Aq. NaHCO3-solution was added and the mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated in vacuo to yield the title compound which was used in the next step without further purification. LCMS (method A) RtA=1.598 min; [M+H]+=484.0.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-fc5b77b3b0be4674b28bfe48085921c4
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09290485B2

反応ノート

読み込み中…

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