3-Bromoaniline → HCID 12969099, compound

HRID 1266273Notes

Reaction equation

HRID 1266273 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[N:10]=2)[N:5]=[CH:4][C:3]=1[C:22]#[N:23].[Br:24][C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=1)[NH2:28].Cl.N1C=CC=CC=1>C(OC(O)C)C>[Br:24][C:25]1[CH:26]=[C:27]([NH:28][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:13][CH2:14][CH2:15][N:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[N:10]=3)[N:5]=[CH:4][C:3]=2[C:22]#[N:23])[CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 115623-BromoanilineHCID 10176127Pyridinium chlorideHCID 12969097HCID 12969097, compound

Product 1

HCID 12969099HCID 12969099, compound

Reagents, catalysts & solvents 1

HCID 101298981-EthoxyethanolSolvent

Procedure

A mixture of 4-chloro-6-(3-morpholin-4-yl-propoxy)-[1,5]naphthyridine-3-carbonitrile (700 mg, 2.10 mmol), 3-bromoaniline (0.458 ml, 4.2 mmol) and pyridine HCl salt (534 mg, 2.2 mmol) in ethoxyethanol (30 ml) was heated at reflux for 6 hrs under argon. After cooling, the solvent was removed by rotary evaporation. The residue was treated with ice water, made basic with NH4OH, and extracted with ethyl acetate. The combined extracts were washed (sat brine), dried (Na2SO4), and concentrated. The oily residue was dissolved in CH2Cl2, and ether and n-hexane were added to form a solid. The title compound, as a yellow solid, was collected and dried. mass spectrum (electrospray, m/e): 469.9 (M+H); IR cm-1: 2224, 1668, 1628; H-NMR δ (DMSO-d6): 1.88 (2H, m), 2.26-2.29 (6H, m), 2.51 (2H, m), 3.49 (2H, m), 4.34 (2H, m), 7.110-7.311 (3H, m), 7.835 (1H, d, C7-H), 8.240 (1H, d, C8-H), 8.556 (1H, s), 8.721 (1H, s, C2-H), 9.850 (1H, s, NH).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hrs under argon
  3. temperatureAfter cooling
  4. customthe solvent was removed by rotary evaporation
  5. additionThe residue was treated with ice water
  6. extractionextracted with ethyl acetate
  7. washThe combined extracts were washed (sat brine)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. dissolutionThe oily residue was dissolved in CH2Cl2
  11. additionether and n-hexane were added
  12. customto form a solid
  13. customThe title compound, as a yellow solid, was collected
  14. customdried

Sources & evidence

ORD record
ord-8994aea2a9324a5b92ab8ba00c1e5f9a
Source dataset
uspto-grants-2003_04
Patent number
US06548496B2

Reaction notes

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