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Potassium Carbonate → tert-Butyl 5-((1-((3-chloroquinolin-6-yl)methyl)-1H-pyrazole-4-carboxamido)methyl)-4,6-dimethylpyridin-2-ylcarbamate

HRID 928456
ノート
印刷プレビュー

反応式

HRID 928456 の反応式
[NH:1]1[CH:5]=[C:4]([C:6]([NH:8][CH2:9][C:10]2[C:11]([CH3:25])=[CH:12][C:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[N:14][C:15]=2[CH3:16])=[O:7])[CH:3]=[N:2]1.CS(O[CH2:31][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[N:38]=[CH:37][C:36]([Cl:42])=[CH:35]2)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:42][C:36]1[CH:37]=[N:38][C:39]2[C:34]([CH:35]=1)=[CH:33][C:32]([CH2:31][N:1]1[CH:5]=[C:4]([C:6]([NH:8][CH2:9][C:10]3[C:11]([CH3:25])=[CH:12][C:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[N:14][C:15]=3[CH3:16])=[O:7])[CH:3]=[N:2]1)=[CH:41][CH:40]=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 3

HCID 11430Potassium CarbonateHCID 58081315tert-Butyl 5-((1H-pyrazole-4-carboxamido)methyl)-4,6-dimethylpyridin-2-ylcarbamateHCID 86661853(3-Chloroquinolin-6-yl)methyl methanesulfonate

生成物 1

HCID 58081248tert-Butyl 5-((1-((3-chloroquinolin-6-yl)methyl)-1H-pyrazole-4-carboxamido)methyl)-4,6-dimethylpyridin-2-ylcarbamate

試薬・触媒・溶媒 1

HCID 180
Acetone
溶媒

実験手順

A solution of tert-Butyl 5-((1H-pyrazole-4-carboxamido)methyl)-4,6-dimethylpyridin-2-ylcarbamate (145 mg, 0.421 mmol), (3-Chloroquinolin-6-yl)methyl methanesulfonate (143 mg, 0.421 mmol 80%) and K2CO3 (291 mg, 2.105 mmol) in Acetone (3 ml) was stirred for 20 h at 50° C. The reaction was quenched with H2O and extracted twice with DCM. The organic layer was dried with Na2SO4, filtered and evaporated to dryness to afford crude title compound. The crude product was purified by preparative HPLC (Macherey-Nagel Nucleosil 250×40 mm, 5 to 100% ACN and 0.1% TFA, flow 40 ml/min) to afford pure title compound. MS (Method V) [M+H]+=521.4.

後処理

  1. customThe reaction was quenched with H2O
  2. extractionextracted twice with DCM
  3. dry with materialThe organic layer was dried with Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto afford crude title compound
  7. customThe crude product was purified by preparative HPLC (Macherey-Nagel Nucleosil 250×40 mm, 5 to 100% ACN and 0.1% TFA, flow 40 ml/min)

出典と根拠

ORDレコード
ord-90d97aef9ba24316b6d5cbd4671c6659
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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