1H-Indazol-6-amine → HCID 9841012, compound

HRID 1595775Notes

Reaction equation

HRID 1595775 reaction equation
Cl[C:2]1[C:11]2[CH:10]=[C:9]3[O:12][CH2:13][CH2:14][O:15][C:8]3=[CH:7][C:6]=2[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[NH2:18][C:19]1[CH:27]=[C:26]2[C:22]([CH:23]=[N:24][NH:25]2)=[CH:21][CH:20]=1.C([O-])(O)=O.[Na+]>CCO>[NH:25]1[C:26]2[C:22](=[CH:21][CH:20]=[C:19]([NH:18][C:2]3[C:11]4[CH:10]=[C:9]5[O:12][CH2:13][CH2:14][O:15][C:8]5=[CH:7][C:6]=4[N:5]=[CH:4][C:3]=3[C:16]#[N:17])[CH:27]=2)[CH:23]=[N:24]1

Participants

5

Reactant 3

HCID 814231H-Indazol-6-amineHCID 516892Sodium BicarbonateHCID 10634199HCID 10634199, compound

Product 1

HCID 9841012HCID 9841012, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.00 g (4.07 mmol) of 9-chloro-2,3-dihydro[1,4]dioxino[2,3-g]quinoline-8-carbonitrile and 0.649 g (4.88 mmol) of 6-aminoindazole in 25 mL of EtOH was refluxed under N2 for 5.7 h. Satd NaHCO3 was added and the solvent was removed. The residue was slurried with H2O, filtered, washed with H2O and cold EtOH and dried. The crude product was boiled with EtOH, filtered and dried in vacuo (50° C.) to yield 1.06 g of 9-(1H-indazol-6-ylamino)-2,3-dihydro[1,4]dioxino[2,3-g]quinoline-8-carbonitrile as tan crystals: mass spectrum (electrospray, m/e): M+H 344.3.

Workup

  1. temperaturewas refluxed under N2 for 5.7 h
  2. customthe solvent was removed
  3. filtrationfiltered
  4. washwashed with H2O and cold EtOH
  5. customdried
  6. filtrationfiltered
  7. customdried in vacuo (50° C.)

Sources & evidence

ORD record
ord-6a4189d5589743aa9d40d3d70939bb0f
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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