Dimethylformamide → [[(6-{[(4-Chlorobenzyl)amino]carbonyl}-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridin-2-yl)methyl](methyl)amino]methyl(phenyl)phosphinic acid

HRID 23620

反応式

HRID 23620 の反応式
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[S:19][C:18]([CH2:20]Cl)=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.CN[CH2:28][P:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:31])[OH:30].C(=O)([O-])[O-].[K+].[K+].[CH3:44][N:45](C=O)C>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[S:19][C:18]([CH2:20][N:45]([O:30][P:29]([CH3:28])([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)=[O:31])[CH3:44])=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:24][CH:25]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 13171109HCID 13171109、化合物HCID 22574363N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

生成物 1

HCID 86595259[[(6-{[(4-Chlorobenzyl)amino]carbonyl}-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridin-2-yl)methyl](methyl)amino]methyl(phenyl)phosphinic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

A mixture of N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (25 mg, 0.063 mmol), 1-(methylamino)methyl(phenyl)phosphinic acid (R. Tyka, Synthesis 1984, 218) (24 mg, 0.0.13 mmol) and potassium carbonate (35 mg, 0.25 mmol) in dry DMF (1.0 mL) and water (0.25 mL) was stirred at 60° C. for 30 minutes, going to a solution. HPLC analysis indicated reaction was complete. The solvent was removed in vacuo, and the resulting white solid was washed with methylene chloride. The solid was dissolved in water (5 mL) and brought to pH 7 with 1.0 M aqueous HCl. After standing in a 0° C. refrigerator overnight, the mixture was filtered, and the collected solid was washed with cold water. Drying in vacuo left the title compound as a white powder (23 mg).

後処理

  1. customreaction
  2. customThe solvent was removed in vacuo
  3. washthe resulting white solid was washed with methylene chloride
  4. dissolutionThe solid was dissolved in water (5 mL)
  5. customAfter standing in a 0° C.
  6. customrefrigerator overnight
  7. filtrationthe mixture was filtered
  8. washthe collected solid was washed with cold water
  9. customDrying in vacuo
  10. waitleft the title compound as a white powder (23 mg)

出典と根拠

ORDレコード
ord-b36533683eaa46b2bf0815affb15a2e6
出典データセット
uspto-grants-2005_02
特許番号
US06852731B2

関連ノート

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