Acetic Acid → 3-Chloro-6-(4-cyclopropylpiperazin-1-yl)pyridazine
Reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1.C(O[C:17]1(O[Si](C)(C)C)[CH2:19][CH2:18]1)C.C(O)(=O)C.C([BH3-])#N.[Na+]>C1COCC1.O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH:17]3[CH2:19][CH2:18]3)[CH2:12][CH2:13]2)=[CH:6][CH:7]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 62 °C
Procedure
3-Chloro-6-piperazin-1-ylpyridazine (9.93 g, 50 mmol) was suspended in THF (80 mL), and water (18.9 mL), [(1-ethoxycyclopropyl)oxy]trimethylsilan (17.423 g, 100 mmol), acetic acid (8.5 mL, 150 mmol) and sodium cyanoborohydride (4.08 g, 65 mmol) were added. The mixture was heated at 62° C. for 16 h, solvents removed in vacuo and the remainder stirred with DCM (100 mL) and water (75 mL). The pH was adjusted to 10, the organic phase was separated, washed with water and dried over magnesium sulphate. Evaporation in vacuo yielded 3-chloro-6-(4-cyclopropylpiperazin-1-yl)pyridazine as a solid which was recrystallized from acetonitrile to yield the product, 8.18 g, 69%.
Workup
- customsolvents removed in vacuo
- customthe organic phase was separated
- washwashed with water
- dry with materialdried over magnesium sulphate
- customEvaporation in vacuo
Sources & evidence
- ORD record
- ord-8072da4933424fddb9e03a81700415a0
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08378097B2
Reaction notes
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