Dimethylformamide → HCID 86696351, compound

HRID 870654Notes

Reaction equation

HRID 870654 reaction equation
[Br:1][C:2]1[N:6]2[N:7]=[C:8](F)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH3:12][N:13]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:14][CH2:15][CH2:16][NH2:17].CN(C=O)C>CCOC(C)=O.O>[Br:1][C:2]1[N:6]2[N:7]=[C:8]([NH:17][CH2:16][CH2:15][CH2:14][N:13]([CH3:12])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 577774N-(3-Aminopropyl)-N-methylanilineHCID 866963183-Bromo-6-fluoroimidazo[1,2-b]pyridazine

Product 1

HCID 86696351HCID 86696351, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 300 mg (1.389 mmol) of the 3-bromo-6-fluoroimidazo[1,2-b]pyridazine, was added N1-methyl-N1-phenylpropane-1,3-diamine (456 mg, 2.778 mmol) Cs2CO3 (903 mg, 2.778 mmol) and 10 mL DMF. This mixture is stirred overnight at rt. It was diluted with 30 mL EtOAc, and 15 mL of water. The organic layer was washed with brine and dried over MgSO4. It was concentrated and purified using silica gel chromatography (ISCO) eluting with 0-10% MeOH/DCM to obtain 301 mg (60%) of product.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over MgSO4
  3. concentrationIt was concentrated
  4. custompurified
  5. washeluting with 0-10% MeOH/DCM

Sources & evidence

ORD record
ord-2d1311ab99bf4b158a2913fc2252087b
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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