Hydrogen Bromide → HCID 178419571, compound

HRID 2274746Notes

Reaction equation

HRID 2274746 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][C@H:11]([CH2:13][NH:14][C:15](=[O:17])[CH3:16])[O:10][C:9]2=[O:18])[CH:5]=[CH:4][C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][NH:26][CH2:27][C:28]2[NH:32][N:31]=[N:30][CH:29]=2)=[CH:21][CH:20]=1.[BrH:33]>C(O)C>[BrH:33].[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][C@H:11]([CH2:13][NH:14][C:15](=[O:17])[CH3:16])[O:10][C:9]2=[O:18])[CH:5]=[CH:4][C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][NH:26][CH2:27][C:28]2[NH:32][N:31]=[N:30][CH:29]=2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 178474856HCID 178474856, compound

Product 1

HCID 178419571HCID 178419571, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred suspension of N-{[(5S)-3-(2-fluoro-4′-{[(1H-1,2,3-triazol-5-ylmethyl)amino]methyl}biphenyl-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide (56.7 mg, 0.129 mmol) in ethanol (1.0 mL) was added 1.0 M hydrogen bromide in ethanol containing 8.77% water (0.39 mL, 0.39 mmol), and the resulting mixture was stirred at room temperature for 60 min. The mixture was then heated to 65° C., stirred for 60 min, cooled to room temperature and stirred for an additional 2 h. The solid was filtered and dried under reduced pressure at 50° C. to afford the title compound (64.5 mg, 94.5%) as a crystalline solid which was characterized by XRPD. FIG. 2 shows a characteristic X-ray powder diffraction (XRPD) pattern of crystalline N-{[(5S)-3-(2-fluoro-4′-{[(1H-1,2,3-triazol-5-ylmethyl)amino]methyl}biphenyl-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide monohydrobromide. Characteristic peaks, expressed in degrees 2θ, are listed in Table 2.

Workup

  1. temperatureThe mixture was then heated to 65° C.
  2. stirringstirred for 60 min
  3. temperaturecooled to room temperature
  4. stirringstirred for an additional 2 h
  5. filtrationThe solid was filtered
  6. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-53dafd559f014ab9b9bb9e8b5fb556b5
Source dataset
uspto-grants-2015_09
Patent number
US09126991B2

Reaction notes

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