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

Reaction equation

HRID 23620 reaction equation
[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

Participants

6

Reactant 4

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

Product 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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-b36533683eaa46b2bf0815affb15a2e6
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Linked notes

Loading…