Sodium hydride → HCID 178427953, compound

HRID 2218413Notes

Reaction equation

HRID 2218413 reaction equation
[Cl:1][C:2]1[C:3]([CH3:21])=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.Cl.Cl[CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH3:21])=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 178427954HCID 178427954, compound

Product 1

HCID 178427953HCID 178427953, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-(6-Chloro-7-methyl-3H-imidazo[4,5-b]pyridin-2-yl)-2-nitrophenol (Example 248) (105 mg, 0.34 mmol), 4-(2-chloroethyl)morpholine hydrochloride (74 mg, 0.40 mmol) and sodium hydride (29 mg, 1.2 mmol) were dissolved in DMF (13 ml). The reaction mixture was stirred at 100° C. overnight and then quenched with water (5 ml) and evaporated. The residue was dissolved in CH3CN (4 ml) and a drop of TFA and purified by HPLC C18. The appropriate fractions were collected and concentrated in vacuo to afford the subtitle compound (100 mg, 60%).

Workup

  1. customquenched with water (5 ml)
  2. customevaporated
  3. dissolutionThe residue was dissolved in CH3CN (4 ml)
  4. customa drop of TFA and purified by HPLC C18
  5. customThe appropriate fractions were collected
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb216632892d4563b23dcaac233fa6bf
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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