1H-Indazol-6-amine → HCID 21704767, compound

HRID 1595776Notes

Reaction equation

HRID 1595776 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:17]#[N:18].[NH2:19][C:20]1[CH:28]=[C:27]2[C:23]([CH:24]=[N:25][NH:26]2)=[CH:22][CH:21]=1.C([O-])(O)=O.[Na+]>CCO>[CH2:13]([O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:15][CH3:16])[N:5]=[CH:4][C:3]([C:17]#[N:18])=[C:2]2[NH:19][C:20]1[CH:28]=[C:27]2[C:23]([CH:24]=[N:25][NH:26]2)=[CH:22][CH:21]=1)[CH3:14]

Participants

5

Reactant 3

HCID 814231H-Indazol-6-amineHCID 516892Sodium BicarbonateHCID 10539447HCID 10539447, compound

Product 1

HCID 21704767HCID 21704767, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.00 g (3.82 mmol) of 4-chloro-6-ethoxy-7-methoxyquinoline-3-carbonitrile and 0.609 g (4.58 mmol) of 6-aminoindazole in 20 mL of EtOH was refluxed under N2 for 8 h. Satd NaHCO3 was added, solvent was removed and the residue was azeotroped twice with EtOH. The solid was slurried with cold EtOH, collected, washed twice with H2O and dried. Recrystallization from EtOH yielded 0.646 g of 6-ethoxy-4-(1H-indazol-6-ylamino)-7-methoxyquinoline-3-carbonitrile as tan crystals: mass spectrum (electrospray, m/e): M+H 359.9.

Workup

  1. temperaturewas refluxed under N2 for 8 h
  2. customsolvent was removed
  3. customthe residue was azeotroped twice with EtOH
  4. customcollected
  5. washwashed twice with H2O
  6. customdried
  7. customRecrystallization from EtOH

Sources & evidence

ORD record
ord-3ca157ae77884c71969ec745b86c5021
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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