Hydrogen Bromide → HCID 178419571, compound

HRID 2274747Notes

Reaction equation

HRID 2274747 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH: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[N:29]=[N:30][NH:31][CH:32]=2)=[CH:21][CH:20]=1.[BrH:33].C(O)(C)C>CO.ClCCl>[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:29][N:30]=[N:31][CH:32]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3776IsopropanolHCID 178474584HCID 178474584, compound

Product 1

HCID 178419571HCID 178419571, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a suspension of N-[3-(2-Fluoro-4′-{[(1H-[1,2,3]triazol-4-ylmethyl)-amino]-methyl}-biphenyl-4-yl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide (20 mg, 0.046 mmol) in 1:1 methanol/dichloromethane (0.6 mL) was added dropwise 0.5 M hydrobromic acid in isopropanol (0.28 mL, 0.14 mmol). The reaction mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure, acetonitrile (0.6 mL) was added and the resulting slurry stirred at room temperature overnight. The solid was filtered and dried to give the title compound (0.6 g, 98%) as a solid which was characterized by XRPD. FIG. 3 shows a characteristic X-ray powder diffraction (XRPD) pattern of amorphous 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.

Workup

  1. customThe solvent was removed under reduced pressure, acetonitrile (0.6 mL)
  2. additionwas added
  3. stirringthe resulting slurry stirred at room temperature overnight
  4. filtrationThe solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-345f616110c849d8b325347653380bf2
Source dataset
uspto-grants-2015_09
Patent number
US09126991B2

Reaction notes

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