Methylamine → HCID 22593809, compound

HRID 389093

Reaction equation

HRID 389093 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=O)=[N:3]1.[Cl-].CO[C:17]1N=C(OC)N=C([N+]2(C)CCOCC2)[N:18]=1.CN>CO>[CH3:17][NH:18][C:11]([C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([CH3:1])[N:3]=1)=[O:13]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 6891051H-Indazole-3-carboxylic acid, 1-methyl-HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride

Product 1

HCID 22593809HCID 22593809, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-methyl-1H-indazole-3-carboxylic acid (2.64 g) was mixed with methanol (20 ml) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium chloride (4.57 g) and methylamine (40% methanol solution, 2.0 ml) were added thereto at room temperature. After stirring at room temperature for 14 hours, the reaction solution was concentrated under reduced pressure. The residue was diluted with ethyl acetate, and the organic layer was washed with water-saturated brine (1:1) and further saturated brine in this order. The organic layer was dried over anhydrous sodium sulfate and was then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20-50:50) to obtain N,1-dimethyl-1H-indazole-3-carboxamide (1.84 g) as a colorless solid.

Workup

  1. additionwere added
  2. customat room temperature
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washthe organic layer was washed with water-saturated brine (1:1) and further saturated brine in this order
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationwas then concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20-50:50)

Sources & evidence

ORD record
ord-bd0a9a070e2d4505aaacb1e4592f208c
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Linked notes

Loading…