P-Anisidine → 6-chloro-N-(4-ethoxyphenyl)-7-methylimidazo[1,2-b]pyridazin-8-amine

HRID 2239824Notes

Reaction equation

HRID 2239824 reaction equation
Cl.Br[C:3]1[C:4]2[N:5]([CH:11]=[CH:12][N:13]=2)[N:6]=[C:7]([Cl:10])[C:8]=1[CH3:9].[CH3:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([NH2:23])=[CH:21][CH:22]=1.COC1C=CC(N)=CC=1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1.O>[Cl:10][C:7]1[C:8]([CH3:9])=[C:3]([NH:23][C:20]2[CH:19]=[CH:18][C:17]([O:16][CH2:15][CH3:14])=[CH:22][CH:21]=2)[C:4]2[N:5]([CH:11]=[CH:12][N:13]=2)[N:6]=1

Participants

7

Reactant 4

HCID 7732P-AnisidineHCID 90764-EthoxyanilineHCID 11430Potassium CarbonateHCID 86611713HCID 86611713, compound

Product 1

HCID 866117156-chloro-N-(4-ethoxyphenyl)-7-methylimidazo[1,2-b]pyridazin-8-amineYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
225 °C

Procedure

(1d variation 1) A mixture of 8-bromo-6-chloro-7-methylimidazo[1,2-b]pyridazine HCl salt (30 mg, 0.1 mmol) from 1c, p-methoxyaniline (20 μL, 0.15 mmol) and K2CO3 (75 mg) were suspended in NMP (600 μL) and heated in a microwave at 225° C. for 15 min. The mixture was cooled to room temperature and then treated with H2O (5 mL). The solid that precipitated out was filtered, washed with water and dried to provide 6-chloro-N-(4-ethoxyphenyl)-7-methylimidazo[1,2-b]pyridazin-8-amine (21 mg, >90% pure by HPLC).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe solid that precipitated out
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-92981fe84f5648f68fcb663cca5f5c04
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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