Water → HCID 10180885, compound

HRID 897279Notes

Reaction equation

HRID 897279 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([Cl:23])[CH:22]=1)[CH2:5][NH:6][C:7]([C:9]1[C:18]([OH:19])=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][N:10]=1)=[O:8].[Br:24]N1C(=O)CCC1=O.O>C(Cl)Cl>[Br:24][C:11]1[N:10]=[C:9]([C:7]([NH:6][CH2:5][C:4]2[CH:20]=[C:21]([Cl:23])[CH:22]=[C:2]([Cl:1])[CH:3]=2)=[O:8])[C:18]([OH:19])=[C:17]2[C:12]=1[CH:13]=[CH:14][CH:15]=[N:16]2

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 9950189HCID 9950189, compound

Product 1

HCID 10180885HCID 10180885, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide from Example 1, Step 3 (1.28 g, 3.69 mmol) in CH2Cl2 (100 ml) at room temperature was added N-bromosuccinimide (0.689 g, 3.87 mmol). The reaction was stirred for 4 hrs and then poured into water. The organic phase was washed with water (3×100 ml), and dried (Na2SO4). The solvent was evaporated in vacuo and the residue triturated with CH2Cl2 to afford the title compound as an off white solid.

Workup

  1. washThe organic phase was washed with water (3×100 ml)
  2. dry with materialdried (Na2SO4)
  3. customThe solvent was evaporated in vacuo
  4. customthe residue triturated with CH2Cl2

Sources & evidence

ORD record
ord-49a313f98fd44dca9600d30b2d8a7888
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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