(R)-4-(6-bromo-2-(4-methoxybenzylamino)quinolin-3-yl)-5-methylmorpholin-3-one → (R)-6-bromo-N-(4-methoxybenzyl)-3-(3-methylmorpholino)quinolin-2-amine

HRID 1028969Notes

Reaction equation

HRID 1028969 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][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:6]([N:22]1[C@H:27]([CH3:28])[CH2:26][O:25][CH2:24][C:23]1=O)=[CH:5]2>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:6]([N:22]1[CH2:23][CH2:24][O:25][CH2:26][C@H:27]1[CH3:28])=[CH:5]2

Participants

3

Reactant 1

HCID 67325496(R)-4-(6-bromo-2-(4-methoxybenzylamino)quinolin-3-yl)-5-methylmorpholin-3-one

Product 1

HCID 71253127(R)-6-bromo-N-(4-methoxybenzyl)-3-(3-methylmorpholino)quinolin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (R)-4-(6-bromo-2-(4-methoxybenzylamino)quinolin-3-yl)-5-methylmorpholin-3-one (0.11 g, 0.241 mmol) in THF (5 mL) was added borane tetrahydrofuran complex, 1.0M in THF (0.482 mL, 0.482 mmol) and the resulting mixture was refluxed for 1 h. Some of the borane-amine complex was observed. The mixture was brought at RT, concentrated and dissolved in MeOH. The mixture was purged with N2 followed by the addition of Pd/C and stirred at RT for 20 min until no more complex was observed. The mixture was filtered through celite and concentrated to give (R)-6-bromo-N-(4-methoxybenzyl)-3-(3-methylmorpholino)quinolin-2-amine that was used without purification.

Workup

  1. temperaturethe resulting mixture was refluxed for 1 h
  2. customwas brought at RT
  3. concentrationconcentrated
  4. dissolutiondissolved in MeOH
  5. customThe mixture was purged with N2
  6. additionfollowed by the addition of Pd/C
  7. filtrationThe mixture was filtered through celite and
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e52d4de55e57438185e5ab174bc0e2ed
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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