1H-Indazol-6-amine → 7-Ethoxy-4-(indazol-6-ylamino)-6-methoxy-quinoline-3-carbonitrile

HRID 1595767Notes

Reaction equation

HRID 1595767 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH3:16])=[C:9]([O:12][CH3:13])[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)C>[CH2:15]([O:14][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:19][C:20]3[CH:28]=[C:27]4[C:23]([CH:24]=[N:25][NH:26]4)=[CH:22][CH:21]=3)=[C:3]([C:17]#[N:18])[CH:4]=[N:5]2)=[CH:10][C:9]=1[O:12][CH3:13])[CH3:16]

Participants

4

Reactant 2

HCID 814231H-Indazol-6-amineHCID 105634734-Chloro-7-ethoxy-6-methoxy-3-quinolinecarbonitrile

Product 1

HCID 102919407-Ethoxy-4-(indazol-6-ylamino)-6-methoxy-quinoline-3-carbonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 500 mg (1.90 mmol) 4-chloro-7-ethoxy-6-methoxy-quinoline-3-carbonitrile, 30 ml ethanol, and 304 mg (2.28 mmol) 6-aminoindazole was heated to reflux under N2. Removed heat at 4 hours and made basic with saturated sodium bicarbonate. Stripped solvents, slurried residue with hexane, collected solids and dried. Washed with water and dried in vacuo, giving 546 mg of tan solid: mass spectrum (electrospray m/e): M+H=359.9.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customRemoved
  4. temperatureheat at 4 hours
  5. customcollected solids
  6. customdried
  7. washWashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-159ba4eba5f34f4c8b7c149474b0e620
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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