Formaldehyde → HCID 58438355, compound

HRID 1972049Notes

Reaction equation

HRID 1972049 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10]([C:12]2[N:13]=[N:14][C:15]([CH2:32][CH2:33][CH2:34][CH3:35])=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:20][CH:19]=3)[CH:17]=2)=[O:11])[CH2:5][CH2:4]1.C=O.[C:38](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:38][N:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10]([C:12]2[N:13]=[N:14][C:15]([CH2:32][CH2:33][CH2:34][CH3:35])=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:20][CH:19]=3)[CH:17]=2)=[O:11])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67372740HCID 67372740, compound

Product 1

HCID 58438355HCID 58438355, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(4-benzyloxy-phenyl)-6-butyl-pyridazine-3-carboxylic acid piperidin-4-ylamide dihydrochloride salt (0.096 mmol, 50 mg) and paraformaldehyde (0.96 mmol, 87 mg) in DCM was stirred for 20 min, and then sodium triacetoxyborohydride (0.96 mmol, 204 mg) was added, and stirring continued over night. The solvent was evaporated and to the residue was added saturated NaHCO3 solution, and extracted with ethyl acetate. The organic layer was washed with water, brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. The resultant product was purified by column chromatography using 5% methanolic solution of ammonia (2.0 M ammonia in methanol) in DCM to provide 5-(4-benzyloxy-phenyl)-6-butyl-pyridazine-3-carboxylic acid (1-methyl-piperidin-4-yl)-amide LCMS: m/z 460.3 [M+2].

Workup

  1. waitcontinued over night
  2. customThe solvent was evaporated and to the residue
  3. additionwas added saturated NaHCO3 solution
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resultant product was purified by column chromatography

Sources & evidence

ORD record
ord-111c0ce34a8c4d41830d236664fb378b
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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