N-bromobutanimide → 7-Bromo-6-{[2,6-dichloro-4-(1-hydroxy-1-methylethyl)phenyl]amino}pyrido[4,3-c]-1,6-naphthyridin-10(9H)-one

HRID 1802493Notes

Reaction equation

HRID 1802493 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(=O)N([Br:36])C(=O)C1>CN(C=O)C>[Br:36][C:24]1[C:23]2[C:14]([NH:13][C:3]3[C:2]([Cl:1])=[CH:7][C:6]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:5][C:4]=3[Cl:12])=[N:15][C:16]3[C:21]([C:22]=2[C:27](=[O:28])[NH:26][CH:25]=1)=[CH:20][N:19]=[CH:18][CH:17]=3

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 594361096-{[2,6-Dichloro-4-(1-hydroxy-1-methylethyl)phenyl]amino}pyrido[4,3-c]-1,6-naphthyridin-10(9H)-one

Product 1

HCID 594360417-Bromo-6-{[2,6-dichloro-4-(1-hydroxy-1-methylethyl)phenyl]amino}pyrido[4,3-c]-1,6-naphthyridin-10(9H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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) (86, 0.21 mmol) in DMF (4 mL) at 0° C. was added NBS (44 mg, 0.25 mmol) and the reaction mixture was stirred for 1.5 hr. The solution was quenched with 10% sodium thiosulfate and saturated NaHCO3 and stirred for 30 min. The reaction mixture was diluted with CH2Cl2 and the layers were separated. The organic layers were dried with MgSO4, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography (100% CH2Cl2 to 65% CH2Cl2/35% MeOH) afforded the desired product.

Workup

  1. customThe solution was quenched with 10% sodium thiosulfate and saturated NaHCO3
  2. stirringstirred for 30 min
  3. additionThe reaction mixture was diluted with CH2Cl2
  4. customthe layers were separated
  5. dry with materialThe organic layers were dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by silica gel chromatography (100% CH2Cl2 to 65% CH2Cl2/35% MeOH)

Sources & evidence

ORD record
ord-d9e5f355ea724c68b126ff8d238302dc
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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