Sodium Carbonate → 3-Bromo-6-[4-[3-[4-(4,5-dihydro-2-oxazolyl)phenoxy]propyl]-1-piperazinyl]pyridazine

HRID 1030928Notes

Reaction equation

HRID 1030928 reaction equation
[Br:1][C:2]1[N:3]=[N:4][C:5](Br)=[CH:6][CH:7]=1.[O:9]1[CH2:13][CH2:12][N:11]=[C:10]1[C:14]1[CH:29]=[CH:28][C:17]([O:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[Br:1][C:2]1[N:3]=[N:4][C:5]([N:25]2[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][CH2:19][O:18][C:17]3[CH:16]=[CH:15][C:14]([C:10]4[O:9][CH2:13][CH2:12][N:11]=4)=[CH:29][CH:28]=3)[CH2:23][CH2:24]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2488523,6-DibromopyridazineHCID 149891791-[3-[4-(4,5-Dihydro-2-oxazolyl)phenoxy]propyl]piperazine

Product 1

HCID 149892973-Bromo-6-[4-[3-[4-(4,5-dihydro-2-oxazolyl)phenoxy]propyl]-1-piperazinyl]pyridazineYield 16.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 4.1 parts of 3,6-dibromopyridazine, 4.34 parts of 1-[3-[4-(4,5-dihydro-2-oxazolyl)phenoxy]propyl]piperazine, 6.4 parts of sodium carbonate and 188 parts of N,N-dimethylformamide was stirred overnight at 65° C. The reaction mixture was poured into ice water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98.5:1.5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 1.1 parts (16.4%) of 3-bromo-6-[4-[3-[4-(4,5-dihydro-2-oxazolyl)phenoxy]propyl]-1-piperazinyl]pyridazine; mp. 169.1° C. (comp. 75).

Workup

  1. extractionthe product was extracted with dichloromethane
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (98.5:1.5 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from 2-propanol
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-de90e4f139464101b6de5f793b517a58
Source dataset
uspto-grants-1992_04
Patent number
US05106973

Reaction notes

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