Tetrahydrofuran → HCID 18387238, compound

HRID 1857798Notes

Reaction equation

HRID 1857798 reaction equation
C1COCC1.[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:23])O[C:14]=2[C:24]([OH:26])=[O:25])=[CH:9][CH:8]=1.Br.[Br:28][CH2:29][CH2:30][CH2:31][NH2:32].C(N(CC)CC)C>CO>[Br:28][CH2:29][CH2:30][CH2:31][N:32]1[C:14]([C:24]([OH:26])=[O:25])=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([CH3:6])=[CH:8][CH:9]=2)[C:22]2[C:17](=[N:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:23]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 787013-Bromopropylamine hydrobromideHCID 18387329HCID 18387329, compound

Product 1

HCID 18387238HCID 18387238, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A THF (5 ml) solution of 5-(4-methylphenyl)-8-oxo-8H-pyrano[3,4-b]pyridine-6-carboxylic acid (150 mg) was dropwise added to a mixture of 3-bromopropylamine hydrobromide (1.5 g), triethylamine (2.0 ml) and methanol (5 ml), and stirred at room temperature for 2 hours. Then, the solvent was removed by distillation. Hydrochloric acid (10 ml) was added to the residue, stirred for 14 hours at room temperature and then concentrated. The resulting concentrate was adjusted the pH to 1 with 1 N-NaOH. The crystals thus precipitated were taken out by filtration and washed with water to obtain 7-(3-bromopropyl)-7,8-dihydro-5-(4-methylphenyl)-8-oxo-6-pyrido[3,4-b]pyridinecarboxylic acid as colorless crystals (131 mg). m.p. 194-196° C. (recrystallized from THF-isopropyl ether) NMR(200 MHz, CDCl3 -DMSO-d6) ppm: 2.30-2.60(2H,m), 2.42(3H,s), 3.54(2H,t,J=6.8 Hz), 4.29(2H,t,J=7.2 Hz), 5.42(1H,bs,--CO2H), 7.20-7.40(4H,m), 7.50(1H,m), 7.64(1H,d,J=8.0 Hz), 8.88(1H,m).

Workup

  1. customThen, the solvent was removed by distillation
  2. additionHydrochloric acid (10 ml) was added to the residue
  3. stirringstirred for 14 hours at room temperature
  4. concentrationconcentrated
  5. concentrationThe resulting concentrate
  6. customThe crystals thus precipitated
  7. filtrationwere taken out by filtration
  8. washwashed with water

Sources & evidence

ORD record
ord-aae53bce224d4fe7ad52acfe9f6dc43a
Source dataset
uspto-grants-2000_11
Patent number
US06147071

Reaction notes

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