Diisopropylethylamine → HCID 67504689, compound

HRID 574287Notes

Reaction equation

HRID 574287 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]([CH2:21][CH2:22][CH3:23])[CH:10]2[CH2:19][C:18]3[CH:17]=[C:16]([OH:20])[CH:15]=[CH:14][C:13]=3[CH2:12][CH2:11]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.Cl[C:34]1[C:43]2[C:38](=[C:39]([O:44][CH3:45])[CH:40]=[CH:41][CH:42]=2)[N:37]=[CH:36][CH:35]=1>C(O)(C)C>[CH3:45][O:44][C:39]1[CH:40]=[CH:41][CH:42]=[C:43]2[C:38]=1[N:37]=[CH:36][CH:35]=[C:34]2[N:4]1[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][N:9]([CH2:21][CH2:22][CH3:23])[CH:10]2[CH2:19][C:18]3[CH:17]=[C:16]([OH:20])[CH:15]=[CH:14][C:13]=3[CH2:12][CH2:11]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 123366624-Chloro-8-methoxyquinolineHCID 45139978HCID 45139978, compound

Product 1

HCID 67504689HCID 67504689, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 9a (0.6 g, 1.89 mmol) and diisopropylethylamine (0.4 mL, 2.08 mmol, 1.1 equiv) in 15 mL isopropanol was added 4-chloro-8-methoxyquinoline (17) (0.366 g, 1.89 mmol, 1 equiv). The mixture was refluxed with stirring for overnight. It was then evaporated and concentrate was dissolved in CH2Cl2 (50 mL) and the solution obtained was washed with 5% NaHCO3 (3×50 mL), brine (2×50 mL), and then dried over Na2SO4. The solution was filtered and evaporated to dryness. The residue was purified through column chromatography using 20% methanol in ethyl acetate to give 18a as white wax (0.66 g, 73% yield). 1H NMR (400 MHz, CDCl3) δ ppm 0.93-0.95 (t, 3H, 4 Hz), 1.75 (m, 3H), 2.11-2.21 (m, 2H), 2.69-3.07 (m, 13H), 3.23 (s, 4H), 3.47 (s, 1H), 4.02 (s, 3H), 6.60 (s, 1H), 6.66-6.68 (d, 1H, J=8 Hz), 6.82-6.84 (t, 2H, J=4 Hz), 6.98-7.00 (d, 1H, J=8 Hz), 7.36-7.42 (t, 1H, J=12 Hz), 7.50-7.52 (d, 1H, J=8 Hz), 8.67-8.68 (d, 1H, J=4 Hz).

Workup

  1. temperatureThe mixture was refluxed
  2. customIt was then evaporated
  3. concentrationconcentrate
  4. dissolutionwas dissolved in CH2Cl2 (50 mL)
  5. customthe solution obtained
  6. washwas washed with 5% NaHCO3 (3×50 mL), brine (2×50 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationThe solution was filtered
  9. customevaporated to dryness
  10. customThe residue was purified through column chromatography

Sources & evidence

ORD record
ord-9e690e2c33cd4bde82aca0f97f7cfcff
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

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