1H-Pyrazol-3-amine, 5-methyl- → HCID 178486652, compound

HRID 2100759Notes

Reaction equation

HRID 2100759 reaction equation
[C:1]([CH2:3][C:4]1[C:9]([C:10](O)=[O:11])=[CH:8][C:7]([C:13]([NH2:15])=[O:14])=[C:6]([O:16][CH3:17])[CH:5]=1)#[N:2].[NH2:18][C:19]1[CH:23]=[C:22]([CH3:24])[NH:21][N:20]=1>C(O)(=O)C>[OH:11][C:10]1[C:9]2[C:4](=[CH:5][C:6]([O:16][CH3:17])=[C:7]([C:13]([NH2:15])=[O:14])[CH:8]=2)[CH:3]=[C:1]([NH:18][C:19]2[CH:23]=[C:22]([CH3:24])[NH:21][N:20]=2)[N:2]=1

Participants

4

Reactant 2

HCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 57799765HCID 57799765, compound

Product 1

HCID 178486652HCID 178486652, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 6-Cyanomethyl-4-methoxy-isophthalamic acid (0.5 g, 2.34 mmol), 3-amino-5-methylpyrazol (0.45 g, 4.68 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. This solution was added dropwise to 30 ml water, and the formed solid was collected and purified by flash column chromatography to give product (0.63 g, 86%). LC-MS: m/e 314 (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 formed solid was collected
  6. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-f4208c2d2220445297c77337bce8047a
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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