Hydrochloric Acid → 6-bromo-3-(3,6-dihydro-2H-pyran-4-yl)quinolin-2-amine

HRID 1028991Notes

Reaction equation

HRID 1028991 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12]CC1C=CC(OC)=CC=1)[C:6]([C:22]1(O)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[CH:5]2.Cl>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH2:12])[C:6]([C:22]1[CH2:27][CH2:26][O:25][CH2:24][CH:23]=1)=[CH:5]2

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 712533944-(6-bromo-2-(4-methoxybenzylamino)quinolin-3-yl)tetrahydro-2H-pyran-4-ol

Product 1

HCID 712533856-bromo-3-(3,6-dihydro-2H-pyran-4-yl)quinolin-2-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

4-(6-Bromo-2-(4-methoxybenzylamino)quinolin-3-yl)tetrahydro-2H-pyran-4-ol (0.250 g, 0.564 mmol) in a mixture of dioxane (4 mL), 5N HCl (4.00 mL, 20.00 mmol) and concentrated HCl (1.00 mL, 32.9 mmol) was heated at 90° C. for 5 h. The reaction was transferred to a microwave reaction vessel and heated in a microwave reactor at 130° C. for 40 min and was concentrated. The crude solid was partitioned between EtOAc and 10% sodium carbonate. The combined organic extracts were washed with water, saturated sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material. The crude material was purified by silica gel chromatography by eluting with 1:30 2M NH3 in MeOH/DCM to provide 6-bromo-3-(3,6-dihydro-2H-pyran-4-yl)quinolin-2-amine as white solid.

Workup

  1. customThe reaction was transferred to a microwave reaction vessel
  2. temperatureheated in a microwave reactor at 130° C. for 40 min
  3. concentrationwas concentrated
  4. customThe crude solid was partitioned between EtOAc and 10% sodium carbonate
  5. washThe combined organic extracts were washed with water, saturated sodium chloride
  6. dry with materialdried over sodium sulfate
  7. filtrationThe solution was filtered
  8. concentrationconcentrated in vacuo
  9. customto give the crude material
  10. customThe crude material was purified by silica gel chromatography
  11. washby eluting with 1:30 2M NH3 in MeOH/DCM

Sources & evidence

ORD record
ord-5235afcd32194907b5ef912ff92140e9
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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