Dimethylamine → HCID 68453327, compound

HRID 2356249Notes

Reaction equation

HRID 2356249 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH3:23])=[N:16][N:15]3[CH:24]=2)=[CH:8][CH:7]=1.[CH2:25]=O.[CH3:27][NH:28][CH3:29]>C(O)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH:19]=[C:18]([CH3:25])[C:17]([O:20][CH2:21][CH2:22][CH3:23])=[N:16][N:15]3[C:24]=2[N:28]([CH3:29])[CH3:27])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 11381836HCID 11381836, compound

Product 1

HCID 68453327HCID 68453327, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-[4-(2-methoxyethoxy)phenyl]-6-propoxyimidazo[1,2-b]pyridazine (327 mg, 1 mmol), paraformaldehyde (200 mg, 6.65 mmol), aqueous dimethylamine (40% w/v, 1.0 mL, 8.5 mmol) and acetic acid (3 mL) was heated at 120° for 22 hours. The mixture was cooled and concentrated. The residue was dissolved in chloroform and extracted thrice with dilute (10%) hydrochloric acid. The combined extracts were basified with aqueous sodium hydroxide solution (25%), the resulting suspension chilled in ice and filtered by suction. The collected solid was washed twice with water and dried at the pump to provide Compound 98 (75 mg) as a beige solid. 1H n.m.r. (CDCl3) δ 1.07, t, J=7.4 Hz, 3H; 1.76-1.96, m, 2H; 2.32, s, 6H; 3.47, s, 3H; 3.74-3.82, m, 2H; 3.87, s, 2H; 4.14-4.22, m, 2H; 4.32, t, J=7.5 Hz, 2H; 6.66, d, J=9.5 Hz, 1H; 7.03, d, J=8.8 Hz, 2H; 7.77, d, J=10.2 Hz, 1H; 7.98, d, J=8.8 Hz, 2H. Mass spectrum (APCI+) m/z 385 (M+H, 60%), 340 (100).

Workup

  1. temperaturewas heated at 120° for 22 hours
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in chloroform
  5. extractionextracted thrice
  6. additionwith dilute (10%) hydrochloric acid
  7. temperaturethe resulting suspension chilled in ice
  8. filtrationfiltered by suction
  9. washThe collected solid was washed twice with water
  10. customdried at the pump

Sources & evidence

ORD record
ord-43e8c8db23304b749d8a270dfe20c43b
Source dataset
uspto-grants-2010_07
Patent number
US07759349B2

Reaction notes

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