1H-Indazol-5-amine → HCID 54724211, compound

HRID 1832103Notes

Reaction equation

HRID 1832103 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])O[C:4](=[O:9])[CH:3]=1.[NH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][N:15]=[CH:14]2>O>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:10]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[CH:14]3)[C:4](=[O:9])[CH:3]=1

Participants

4

Reactant 2

HCID 880121H-Indazol-5-amineHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54724211HCID 54724211, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-hydroxy-6-methyl-2-pyrone (3.75 g, 0.029 mol) and 5-aminoindazole (4.0 g, 0.03 mol) in water (70 ml) was heated at 90° C. under argon for 1 h. The mixture was cooled, decanted the supernatant and residue was triturated with ethanol, cooled and filtered the solid. It was washed with cold ethanol, and dried. 1H NMR (CD3OD/400 MHz) δ 8.11 (s, 1H), 7.64 (m, 2H), 7.18 (d, 1H, J=2.0 Hz), 7.16 (d, 1H, J=2.0 Hz), 6.07 (m, 1H), 5.81 (d, 1H, J=2.8 Hz), and 1.94 (s, 3H); ES-HRMS m/z 242.0962 (M+H calcd for C13H12N3O2 requires 242.0924).

Workup

  1. temperatureThe mixture was cooled
  2. customdecanted the supernatant and residue
  3. customwas triturated with ethanol
  4. temperaturecooled
  5. filtrationfiltered the solid
  6. washIt was washed with cold ethanol
  7. customdried

Sources & evidence

ORD record
ord-b384ec30a1cc48f0be4ac666907e5c7d
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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