Formaldehyde → HCID 56836167, compound

HRID 591207Notes

Reaction equation

HRID 591207 reaction equation
[CH2:1]([C:8]1([C:13]2[CH:14]=[C:15]([CH:27]=[CH:28][CH:29]=2)[CH2:16][NH:17][S:18]([C:21]2[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=2)(=[O:20])=[O:19])[CH2:12][CH2:11][NH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:30]=O>CO.[Pd]>[CH2:1]([C:8]1([C:13]2[CH:14]=[C:15]([CH:27]=[CH:28][CH:29]=2)[CH2:16][NH:17][S:18]([C:21]2[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=2)(=[O:20])=[O:19])[CH2:12][CH2:11][N:10]([CH3:30])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 56836106HCID 56836106, compound

Product 1

HCID 56836167HCID 56836167, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-methyl-1H-pyrazole-4-sulfonic acid 3-(3-benzyl-pyrrolidin-3-yl)benzylamide (example 67, 108 mg, 0.26 mmol) and formaldehyde (37% in water, 0.2 ml, 2.6 mmol) in methanol (10 ml) was added palladium on charcoal (10%, 10 mg). Hydrogenation was performed at room temperature over night. The mixture was filtered and the solvent evaporated. The residue was diluted with dichloromethane, extracted with water, dried over Na2CO3. The solvent was evaporated to give 41 mg of product. Re-extraction of the aqueous layer afforded further 38 mg of product as a clear oil.

Workup

  1. waitHydrogenation was performed at room temperature over night
  2. filtrationThe mixture was filtered
  3. customthe solvent evaporated
  4. additionThe residue was diluted with dichloromethane
  5. extractionextracted with water
  6. dry with materialdried over Na2CO3
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-8caa25de7b064676ba17d2f6a0b0bcfe
Source dataset
uspto-grants-2016_01
Patent number
US09238619B2

Reaction notes

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