Hydrogen Bromide → 4-{[1-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1H-pyrazol-4-yl]carbonyl}morpholine monohydrobromide

HRID 1928666Notes

Reaction equation

HRID 1928666 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:23])[CH:19]=[N:18]2)=[CH:13][CH:12]=1.[BrH:30]>C(O)C>[BrH:30].[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([C:22]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)=[O:23])[CH:19]=[N:18]2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 42601503Enerisant

Product 1

HCID 669338524-{[1-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1H-pyrazol-4-yl]carbonyl}morpholine monohydrobromide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 4-{[1-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1H-pyrazol-4-yl]carbonyl}morpholine obtained in Example 6-(2) (1.0 g) in ethanol (5 mL), a solution of hydrobromic acid in ethanol (1.5 M, 2.0 mL) was added and stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, followed by addition of an ethanol:methanol solution (95:5, 10 mL) to give a solution. This solution was stirred for 3 hours while cooling in an ice bath. The precipitated solid was collected by filtration and dried to give the titled compound (1.1 g) as a colorless powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionfollowed by addition of an ethanol
  3. custommethanol solution (95:5, 10 mL) to give a solution
  4. stirringThis solution was stirred for 3 hours
  5. temperaturewhile cooling in an ice bath
  6. filtrationThe precipitated solid was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-403722793f314e9da2cf45dc0656287b
Source dataset
uspto-grants-2012_05
Patent number
US08183387B2

Reaction notes

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