3-Aminophenol → 6-bromo-2-(3-hydroxyphenyl)amino-N-(5-methyl-3-phenylisoxazol-4-yl)-4-quinolinecarboxamide

HRID 1678313Notes

Reaction equation

HRID 1678313 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](Cl)[CH:6]=[C:5]2[C:13]([NH:15][C:16]1[C:17]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:18][O:19][C:20]=1[CH3:21])=[O:14].[NH2:28][C:29]1[CH:30]=[C:31]([OH:35])[CH:32]=[CH:33][CH:34]=1>C(O)C.C(N(CC)CC)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=1)[CH:6]=[C:5]2[C:13]([NH:15][C:16]1[C:17]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:18][O:19][C:20]=1[CH3:21])=[O:14]

Participants

6

Reactant 2

HCID 115683-AminophenolHCID 86598224HCID 86598224, compound

Product 1

HCID 600079196-bromo-2-(3-hydroxyphenyl)amino-N-(5-methyl-3-phenylisoxazol-4-yl)-4-quinolinecarboxamideYield 85.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

The solution of 6-bromo-2-chloro-N-(5-methyl-3-phenylisoxazol-4-yl)-4-quinolinecarboxamide (50 mg) and 3-aminophenol (50 mg) in ethanol (2 mL) and triethylamine (0.1 mL) was microwaved at 170° C. for one hour. The reaction mixture was then diluted with ethyl acetate (60 mL). The organic solution was washed with water (60 mL), 1N HCl aqueous solution (2×60 mL), separated, dried, evaporated and re-crystallized from ethyl acetate and hexanes to give 6-bromo-2-(3-hydroxyphenyl)amino-N-(5-methyl-3-phenylisoxazol-4-yl)-4-quinolinecarboxamide (50 mg) as a yellow solid. 1H NMR (acetone-d6): δ 2.53 (s, 3H), 6.72 (d, J=6.9 Hz, 1H), 7.15 (d, J=7.8 Hz, 1H), 7.26 (t, J=7.8 Hz, 1H), 7.51 (m, 4H), 7.60 (s, 1H), 7.78 (m, 3H), 7.87 (d, J=9.0 Hz, 1H), 8.15 (d, J=2.1 Hz, 1H), 8.70 (br, 1H), 9.77 (br, 1H); LCMS: ret. time: 25.49 min.; purity: 1100%; MS (m/e): 514.91 (M+).

Workup

  1. washThe organic solution was washed with water (60 mL), 1N HCl aqueous solution (2×60 mL)
  2. customseparated
  3. customdried
  4. customevaporated
  5. customre-crystallized from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-8f86c503214f488791d5f22e210456eb
Source dataset
uspto-grants-2011_08
Patent number
US08008501B2

Reaction notes

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