1H-Pyrazol-3-amine, 5-methyl- → HCID 178486653, compound

HRID 2100754Notes

Reaction equation

HRID 2100754 reaction equation
[C:1]([CH2:3][C:4]1[C:9]([C:10](O)=[O:11])=[CH:8][C:7]([C:13]([N:15]([CH3:17])[CH3:16])=[O:14])=[C:6]([O:18][CH3:19])[CH:5]=1)#[N:2].[NH2:20][C:21]1[CH:25]=[C:24]([CH3:26])[NH:23][N:22]=1>C(O)(=O)C>[CH3:16][N:15]([CH3:17])[C:13]([C:7]1[CH:8]=[C:9]2[C:4]([CH:3]=[C:1]([NH:20][C:21]3[CH:25]=[C:24]([CH3:26])[NH:23][N:22]=3)[N:2]=[C:10]2[OH:11])=[CH:5][C:6]=1[O:18][CH3:19])=[O:14]

Participants

4

Reactant 2

HCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 57799630HCID 57799630, compound

Product 1

HCID 178486653HCID 178486653, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 6-Cyanomethyl-4-methoxy-N,N-dimethyl-isophthalamic acid (2.0 g, 7.6 mmol), 3-amino-5-methylpyrazol (1.5 g, 15.44 mmol), acetic acid (10 ml) were sealed in microwave process vial (20 ml). The mixture was heated at 130° C. for 30 minutes under microwave irradiation. After removal of acetic acid, the residue was dissolved in 1.5 ml MeOH, and this solution was added dropwise to 30 ml water. After stirred for 1 hour, the solid was collected and was purified by flash column chromatography to give product (2.2 g, 85%). LC-MS: m/e 342 (MH+).

Workup

  1. customwere sealed in microwave process vial (20 ml)
  2. customAfter removal of acetic acid
  3. dissolutionthe residue was dissolved in 1.5 ml MeOH
  4. additionthis solution was added dropwise to 30 ml water
  5. customthe solid was collected
  6. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-83135e71faa54c288857eb4bf2fc2bb0
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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