Sodium Sulfite → HCID 178458488, compound

HRID 1802492Notes

Reaction equation

HRID 1802492 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][C:14]1[C:23]2[CH:24]=[CH:25][NH:26][C:27](=[O:28])[C:22]=2[C:21]2[C:16](=[CH:17][CH:18]=[N:19][CH:20]=2)[N:15]=1.C1C=C(Cl)C=C(C(OO)=[O:37])C=1.S([O-])([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[NH:13][C:14]1[C:23]2[CH:24]=[CH:25][NH:26][C:27](=[O:28])[C:22]=2[C:21]2[C:16](=[CH:17][CH:18]=[N+:19]([O-:37])[CH:20]=2)[N:15]=1

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 594361096-{[2,6-Dichloro-4-(1-hydroxy-1-methylethyl)phenyl]amino}pyrido[4,3-c]-1,6-naphthyridin-10(9H)-one

Product 1

HCID 178458488HCID 178458488, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-{[2,6-dichloro-4-(1-hydroxy-1-methylethyl)phenyl]amino}pyrido[4,3-c]-1,6-naphthyridin-10(9H)-one (Example 146, Step 1) (30 mg, 0.07 mmol) in CH2Cl2 (3 mL) at 0° C. was added m-CPBA (40.5 mg, 0.18 mmol, 77% max) and stirred for 2 hr. 10% Sodium sulfite and saturated NaHCO3 were added and stirred for 30 min. The solution was extracted with 3:1 CHCl3/iPrOH, dried with MgSO4, filtered, and concentrated under reduced pressure. Column chromatography (100% CH2Cl2 to 30% MeOH, 70% CH2Cl2) provided the desired product.

Workup

  1. stirringstirred for 30 min
  2. extractionThe solution was extracted with 3:1 CHCl3/iPrOH
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3f2c3d42665740c1b5ce2a06049007ad
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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