Sodium hydride → HCID 59320211, compound

HRID 655295Notes

Reaction equation

HRID 655295 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][C:16]([C:22]3[CH:23]=[N:24][NH:25][CH:26]=3)=[CH:15]4)=[N:9][N:10]=2)[N:7]=1.[H-].[Na+].Br[CH2:30][C:31]([NH2:33])=[O:32]>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][C:16]([C:22]3[CH:23]=[N:24][N:25]([CH2:30][C:31]([NH2:33])=[O:32])[CH:26]=3)=[CH:15]4)=[N:9][N:10]=2)[N:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 59320245HCID 59320245, compound

Product 1

HCID 59320211HCID 59320211, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

6-(6-Methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-3-(1H-pyrazol-4-yl)-quinoline (65 mg, 0.19 mmol, 1 equiv) was dissolved in dimethylformamide (0.5 mL) and NaH (60% in oil, 1.2 equiv, 0.228 mmol, 9 mg) was added. The solution was stirred under nitrogen for 30 min and then 2-bromoacetamide (26 mg, 0.19 mmol, 1 equiv) was added and the solution heated at 90° C. for 18 h. The product was extracted into dichloromethane and washed with water. The organic phase was concentrated to dryness to afford the title compound (40 mg, 52% yield). Analytical data presented in Table 2.

Workup

  1. extractionThe product was extracted into dichloromethane
  2. washwashed with water
  3. concentrationThe organic phase was concentrated to dryness

Sources & evidence

ORD record
ord-9bf470a0117f4122ba0770f464099b4d
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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