Formaldehyde → HCID 46181594, compound

HRID 1844618Notes

Reaction equation

HRID 1844618 reaction equation
[CH2:1]=O.[C:3]([C:7]1[CH:8]=[C:9]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])[C:10]([O:37][CH3:38])=[C:11]([NH:13][C:14](=[O:36])[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([O:22][C:23]3[CH:28]=[C:27]([CH2:29][CH:30]4[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]4)[N:26]=[CH:25][N:24]=3)[CH:16]=2)[CH:12]=1)([CH3:6])([CH3:5])[CH3:4].[H][H]>[Pd].CO>[C:3]([C:7]1[CH:8]=[C:9]([NH:39][S:40]([CH3:43])(=[O:41])=[O:42])[C:10]([O:37][CH3:38])=[C:11]([NH:13][C:14](=[O:36])[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([O:22][C:23]3[CH:28]=[C:27]([CH2:29][CH:30]4[CH2:31][CH2:32][N:33]([CH3:1])[CH2:34][CH2:35]4)[N:26]=[CH:25][N:24]=3)[CH:16]=2)[CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 46180980HCID 46180980, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 46181594HCID 46181594, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

40 μl Paraformaldehyde (37% in water) and 30 mg palladium on activated charcoal (10%) are added to 260 mg N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-4-methyl-3-(6-piperidin-4-ylmethyl-pyrimidin-4-yloxy)-benzamide in 10 ml of methanol and the reaction mixture is hydrogenated at ambient temperature and a partial hydrogen pressure of 4 bar. After the uptake of hydrogen has ended the catalyst is suction filtered and the filtrate is evaporated down. The flask residue is chromatographed on aluminium oxide with dichloromethane/methanol (99:1→95:5) as eluant.

Workup

  1. customis hydrogenated at ambient temperature
  2. filtrationfiltered
  3. customthe filtrate is evaporated down
  4. customThe flask residue is chromatographed on aluminium oxide with dichloromethane/methanol (99:1→95:5) as eluant

Sources & evidence

ORD record
ord-73d755e010454cb6ab86b3b976455766
Source dataset
uspto-grants-2015_02
Patent number
US08946438B2

Reaction notes

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