Water → HCID 17986355, compound

HRID 970420Notes

Reaction equation

HRID 970420 reaction equation
Cl.[Br:2][C:3]1[C:4]([NH:10][CH2:11][CH2:12][CH2:13][NH2:14])=[N:5][C:6]([Cl:9])=[N:7][CH:8]=1.[N+:15]([C:18]1[CH:19]=[C:20]([S:24](Cl)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1)([O-:17])=[O:16].O.C(N(CC)CC)C>CC(C)=O>[Br:2][C:3]1[C:4]([NH:10][CH2:11][CH2:12][CH2:13][NH:14][S:24]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([N+:15]([O-:17])=[O:16])[CH:19]=2)(=[O:25])=[O:26])=[N:5][C:6]([Cl:9])=[N:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 86760589HCID 86760589, compound

Product 1

HCID 17986355HCID 17986355, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 530 mg (1.76 mmol) of N-(5-bromo-2-chloro-pyrimidin-4-yl)-propane-1,3-diamine hydrochloride and 352 mg (1.60 mmol) of 3-nitrobenzenesulfonyl chloride in 20 ml of acetone/6 ml of water is mixed at room temperature with 1 ml of triethylamine. After 2.5 hours, the organic solvent is drawn off in a rotary evaporator. After water (20 ml) is added, it is extracted with ethyl acetate. The combined organic phases are washed with citric acid (10%), saturated NaHCO3 solution as well as saturated NaCl solution, dried (Na2SO4), filtered and concentrated by evaporation. 633 mg (1.41 mmol, corresponding to 87% of theory) of the product is obtained.

Workup

  1. customthe organic solvent is drawn off in a rotary evaporator
  2. additionAfter water (20 ml) is added
  3. extractionit is extracted with ethyl acetate
  4. washThe combined organic phases are washed with citric acid (10%), saturated NaHCO3 solution as well as saturated NaCl solution
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. custom633 mg (1.41 mmol, corresponding to 87% of theory) of the product is obtained

Sources & evidence

ORD record
ord-465e1fd39bdb449e81721dee66544cf4
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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