Phosphorus oxychloride → HCID 66926141, compound

HRID 2405038Notes

Reaction equation

HRID 2405038 reaction equation
[CH:1]([N:4]([CH2:8]C)[CH:5](C)C)(C)C.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:38])[CH2:18][N:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=[C:20]2[C:28]2[C:29]([NH:33][CH2:34][CH2:35][C:36]#[N:37])=[N:30][O:31][N:32]=2)=[CH:13][CH:12]=1.P(Cl)(Cl)(Cl)=O.[Cl-].[NH4+]>CN(C)C=O>[C:36]([CH2:35][CH2:34][NH:33][C:29]1[C:28]([C:20]2[N:19]([CH2:18][C:17]([C:14]3[CH:13]=[CH:12][C:11]([N:10]=[CH:1][N:4]([CH3:8])[CH3:5])=[CH:16][CH:15]=3)=[O:38])[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=2)=[N:32][O:31][N:30]=1)#[N:37]

Participants

6

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 11176685798577-91-0

Product 1

HCID 66926141HCID 66926141, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 0.05 ml N,N-diisopropylethylamine in 1 mL of N,N-dimethylformamide is slowly added to a solution of 116 mg (0.3 mmol) 3-(4-{1-[2-(4-amino-phenyl)-2-oxo-ethyl]-1H-benzoimidazol-2-yl}-furazan-3-ylamino)-propionitrile and 459 mg (0.3 mmol) phosphorus oxychloride in 3 mL of N,N-dimethylformamide at −10° C. After the addition, the mixture is allowed to warm to room temperature and stirred for three days. Then, saturated aqueous ammoniumchloride solution is added and the reaction mixture is extracted with dichloromethane. A precipitate is formed in the dichloromethane phase. This precipitate is collected by filtration, washed with water and dichloromethane, and dried under reduced pressure. The residue is solved in acetonitrile and the solution is added to a 2 N solution of sodium hydroxide in water at 0° C. The resulting pH value is above 11. The mixture is stirred at room temperature for 1 h. The formed precipitate is collected by filtration, washed with water and acetonitrile, and dried under reduced pressure to provide 89 mg of the desired product.

Workup

  1. additionAfter the addition
  2. extractionthe reaction mixture is extracted with dichloromethane
  3. customA precipitate is formed in the dichloromethane phase
  4. filtrationThis precipitate is collected by filtration
  5. washwashed with water and dichloromethane
  6. customdried under reduced pressure
  7. additionthe solution is added to a 2 N solution of sodium hydroxide in water at 0° C
  8. stirringThe mixture is stirred at room temperature for 1 h
  9. filtrationThe formed precipitate is collected by filtration
  10. washwashed with water and acetonitrile
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-d71f3afa6d7f4db8bed9d351d1f7ff7c
Source dataset
uspto-grants-2014_08
Patent number
US08802858B2

Reaction notes

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