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Phenol → HCID 10160432、化合物

HRID 897280
ノート
印刷プレビュー

反応式

HRID 897280 の反応式
Br[C:2]1[N:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)=[O:13])[C:9]([OH:24])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:25]1([OH:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C([O-])([O-])=O.[Na+].[Na+]>CN1C(=O)N(C)CCC1>[Cl:23][C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([Cl:22])[CH:19]=1)[CH2:15][NH:14][C:12]([C:10]1[C:9]([OH:24])=[C:8]2[C:3]([CH:4]=[CH:5][CH:6]=[N:7]2)=[C:2]([O:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:11]=1)=[O:13]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 996PhenolHCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 10180885HCID 10180885、化合物

生成物 1

HCID 10160432HCID 10160432、化合物

試薬・触媒・溶媒 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-溶媒

実験手順

To a solution of 5-bromo-N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide from Example 50 (26 mg, 0.068 mmol), phenol (28 mg, 0.304 mmol) and cesium carbonate (198 mg, 0.608 mmol) in DMPU (0.25 ml) was heated at 140C for 8 hrs. The reaction was poured into sat aq. Na2CO3 and extracted with CHCl3. The organic phase was washed with water and dried (Na2SO4). The solvent was evaporated in vacuo and the residue dissolved in DMF (0.7 ml) and purified by preparative HPLC. (Gilson semi preparative HPLC system and a YMC Combiprep Pro Column (50×20 mm I.D., C18, S-5 um, 120A) eluting with 5-95% acetonitrile/water (0.1% TFA) at 15 ml/min) to afford the title compound after lyophilization.

後処理

  1. additionThe reaction was poured
  2. extractionextracted with CHCl3
  3. washThe organic phase was washed with water
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated in vacuo
  6. dissolutionthe residue dissolved in DMF (0.7 ml)
  7. custompurified by preparative HPLC
  8. wash(Gilson semi preparative HPLC system and a YMC Combiprep Pro Column (50×20 mm I.D., C18, S-5 um, 120A) eluting with 5-95% acetonitrile/water (0.1% TFA) at 15 ml/min)

出典と根拠

ORDレコード
ord-386a1c819b194ed9b959d97037d619a5
出典データセット
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06921759B2

反応ノート

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