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

반응식

HRID 23620 반응식
[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

참가 물질

6

반응물 4

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

생성물 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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b36533683eaa46b2bf0815affb15a2e6
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852731B2

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