5-Amino-2-methylphenol → HCID 12969098, compound

HRID 1266272Notes

Reaction equation

HRID 1266272 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].[NH2:24][C:25]1[CH:30]=[C:29]([OH:31])[C:28]([CH3:32])=[CH:27][CH:26]=1.Cl.N1C=CC=CC=1>C(OC(O)C)C>[OH:31][C:29]1[CH:30]=[C:25]([NH:24][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:26]=[CH:27][C:28]=1[CH3:32]

Participants

5

Reactant 3

HCID 178185-Amino-2-methylphenolHCID 10176127Pyridinium chlorideHCID 12969097HCID 12969097, compound

Product 1

HCID 12969098HCID 12969098, 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 (400 mg, 1.202 mmol), 5-amino cresol (222 mg, 1.8 mmol) and pyridine HCl salt (208 mg, 1.8 mmol) in ethoxyethanol (20 ml) was heated at reflux for 6 hrs under argon. After cooling, the solvent was removed by rotary evaporation. The residue was dissolved in ethyl acetate and treated with sat NaHCO3. The ethyl acetate layer was separated and the aqueous layer was extracted with ethyl acetate. The combined extracts were washed (sat NaHCO3 aq sol, brine), dried (Na2SO4), and concentrated. The residue was triturated with CH2Cl2, and ether and hexane were added to form a solid. The yellow solid was collected (200 mg, 40%) and dried. mass spectrum (electrospray, m/e): 420 (M+H); IR cm-1: 3322, 2226, 1628.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hrs under argon
  3. temperatureAfter cooling
  4. customthe solvent was removed by rotary evaporation
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. additiontreated with sat NaHCO3
  7. customThe ethyl acetate layer was separated
  8. extractionthe aqueous layer was extracted with ethyl acetate
  9. washThe combined extracts were washed (sat NaHCO3 aq sol, brine)
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated
  12. customThe residue was triturated with CH2Cl2, and ether and hexane
  13. additionwere added
  14. customto form a solid
  15. customThe yellow solid was collected (200 mg, 40%)
  16. customdried

Sources & evidence

ORD record
ord-2a9f75e6348e4076bf99f344614c56d6
Source dataset
uspto-grants-2003_04
Patent number
US06548496B2

Reaction notes

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