1H-Indazol-6-amine → 4-(1H-indazol-6-ylamino)-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochloride

HRID 393632Notes

Reaction equation

HRID 393632 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][CH:4]=1.[NH2:20][C:21]1[CH:29]=[C:28]2[C:24]([CH:25]=[N:26][NH:27]2)=[CH:23][CH:22]=1>CC(O)CCC>[ClH:2].[NH:27]1[C:28]2[C:24](=[CH:23][CH:22]=[C:21]([NH:20][C:3]3[C:12]4[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:10]([O:13][CH3:14])[CH:11]=4)[N:6]=[CH:5][CH:4]=3)[CH:29]=2)[CH:25]=[N:26]1

Participants

4

Reactant 2

HCID 814231H-Indazol-6-amineHCID 226466534-Chloro-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochloride

Product 1

HCID 226465864-(1H-indazol-6-ylamino)-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochlorideYield 54.8%

Reagents, catalysts & solvents 1

HCID 223862-PentanolSolvent

Procedure

A solution of 4-chloro-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochloride (300 mg, 1 mmol) (prepared as described for the starting material in Example 5), and 6-aminoindazole (130 mg, 0.97 mmol) in 2-pentanol (10 ml) was heated at reflux for 3 hours. The precipitate was collected by filtration, washed with acetone and dried under vacuum. The residue was purified by reverse phase column chromatography eluting with methanol/water containing 1% acetic acid (40/60). Concentrated hydrochloric acid (5 drops) was added to the combined fractions of the product and the volatiles were removed by evaporation to give 4-(1H-indazol-6-ylamino)-6-methoxy-7-(2-methoxyethoxy)quinoline hydrochloride (213 mg, 54%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with acetone
  5. customdried under vacuum
  6. customThe residue was purified by reverse phase column chromatography
  7. washeluting with methanol/water containing 1% acetic acid (40/60)
  8. additionConcentrated hydrochloric acid (5 drops) was added to the combined fractions of the product
  9. customthe volatiles were removed by evaporation

Sources & evidence

ORD record
ord-2225e964505b49b796e9fe81bcda1d5a
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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