Calcium Chloride → HCID 57597297, compound

HRID 1926046Notes

Reaction equation

HRID 1926046 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:18]3[C:19](=[CH:23][N:24]([C:26]4[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][CH:27]=4)[N:25]=3)[N:20]=[CH:21][N:22]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1.[Cl-].[Ca+2].[Cl-]>C(O)C.O>[NH2:32][C:29]1[CH:30]=[CH:31][C:26]([N:24]2[CH:23]=[C:19]3[N:20]=[CH:21][N:22]=[C:17]([NH:16][C:4]4[CH:5]=[CH:6][C:7]([O:8][C:9]5[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=5)=[C:2]([CH3:1])[CH:3]=4)[C:18]3=[N:25]2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 5284359Calcium ChlorideHCID 57597178HCID 57597178, compound

Product 1

HCID 57597297HCID 57597297, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}-2-(4-nitrophenyl)-2H-pyrazolo[4,3-d]pyrimidin-7-amine (200 mg) in a mixed solvent of ethanol/water (9:1, 6 mL) was added calcium chloride (90%, 28 mg) and the mixture was stirred at 100° C. for 10 min. Reduced iron (90%, 164 mg) was added at room temperature, and the mixture was stirred at 100° C. for 5 hrs. After the completion of the reaction, the reaction mixture was filtered (celite), and the filtrate was concentrated under reduced pressure. Water was added to the residue and the mixture was diluted with ethyl acetate and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methylene chloride=10/1) to give the title compound (140 mg) as a white solid.

Workup

  1. stirringthe mixture was stirred at 100° C. for 5 hrs
  2. customAfter the completion of the reaction
  3. filtrationthe reaction mixture was filtered (celite)
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionWater was added to the residue
  6. additionthe mixture was diluted with ethyl acetate
  7. washwashed with water and saturated brine
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (ethyl acetate/methylene chloride=10/1)

Sources & evidence

ORD record
ord-7522943401824bb680ab9e791da51948
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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