Formaldehyde → HCID 58438396, compound

HRID 2168662Notes

Reaction equation

HRID 2168662 reaction equation
Cl.Cl.[CH2:3]([C:7]1[N:12]=[N:11][C:10]([O:13][CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH:15]2[CH2:20][OH:21])=[CH:9][C:8]=1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:24][CH:23]=1)[CH2:4][CH2:5][CH3:6].C=O.[C:37](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.C(Cl)Cl>[CH2:3]([C:7]1[N:12]=[N:11][C:10]([O:13][CH:14]2[CH2:19][CH2:18][N:17]([CH3:37])[CH2:16][CH:15]2[CH2:20][OH:21])=[CH:9][C:8]=1[C:22]1[CH:23]=[CH:24][C:25]([O:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:26][CH:27]=1)[CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67373250HCID 67373250, compound

Product 1

HCID 58438396HCID 58438396, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of {4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-piperidin-3-yl}-methanol dihydrochloride (0.059 mmol, 30 mg), 37% paraformaldehyde (0.205 mmol, 16 mg), and 1 drop of acetic acid in 3 mL of DCM was stirred for 5 min then added sodium triacetoxyborohydride (0.205 mmol, 43 mg) and continued stirring for 0.5 h at room temperature. Quenched with water, solvent was evaporated, the residue was diluted with ethyl acetate, and then washed with saturated NaHCO3 solution, brine. The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure. The resultant residue was purified by column chromatography using 5% methanolic solution of ammonia (2.0 M ammonia in methanol) in DCM to provide {4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-1-methyl-piperidin-3-yl}-methanol.

Workup

  1. customQuenched with water, solvent
  2. customwas evaporated
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with saturated NaHCO3 solution, brine
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resultant residue was purified by column chromatography

Sources & evidence

ORD record
ord-6981f2d7504e4613a609aef2e8fe903b
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

Loading…