Calcium Chloride → HCID 69214348, compound

HRID 2218407Notes

Reaction equation

HRID 2218407 reaction equation
[Cl:1][C:2]1[C:3]([Cl:29])=[C:4]2[NH:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[C:13]([N+:26]([O-])=O)[CH:12]=3)=[N:8][C:5]2=[N:6][CH:7]=1.[Cl-].[Cl-].[Ca+2]>CCO.[Zn]>[Cl:1][C:2]1[C:3]([Cl:29])=[C:4]2[NH:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)=[C:13]([CH:12]=3)[NH2:26])=[N:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 5284359Calcium ChlorideHCID 69209154HCID 69209154, compound

Product 1

HCID 69214348HCID 69214348, compoundYield 1.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

6,7-Dichloro-2-{4-[2-(4-morpholinyl)ethoxy]-3-nitrophenyl}-1H-imidazo[4,5-b]pyridine (Example 246) (200 mg), zinc powder (200 mg) and anhydrous CaCl2 (500 mg) were mixed in 95% EtOH (20 ml) and heated (70° C., 4 h). The reaction mixture was allowed to cool and then filtered and evaporated in vacuo. The residue was dissolved in acetonitrile and subjected to semi-preparative HPLC-C18. The appropriate fraction was evaporated in vacuo and the residue dissolved in EtOAc (5 ml). This solution was washed with saturated aqueous NaHCO3 (5 ml) and brine (2 ml). The organic phase was dried (MgSO4) and evaporated in vacuo to afford the pure product (2 mg, 1%).

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. dissolutionThe residue was dissolved in acetonitrile
  5. customThe appropriate fraction was evaporated in vacuo
  6. dissolutionthe residue dissolved in EtOAc (5 ml)
  7. washThis solution was washed with saturated aqueous NaHCO3 (5 ml) and brine (2 ml)
  8. dry with materialThe organic phase was dried (MgSO4)
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-6faad0cbd51044038b037df089711cdc
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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