Hydrochloric Acid → HCID 178519200, compound

HRID 2199776Notes

Reaction equation

HRID 2199776 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:23]2[CH2:27][CH:26]([CH2:28][OH:29])[O:25][C:24]2=[O:30])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[N:10][C:11]([NH:14][C:15]2[N:16]=[N:17][N:18](COC)[CH:19]=2)=[CH:12][CH:13]=1.Cl>O1CCCC1>[NH:18]1[CH:19]=[C:15]([NH:14][C:11]2[N:10]=[CH:9][C:8]([C:7]3[CH:6]=[CH:5][C:4]([N:23]4[CH2:27][CH:26]([CH2:28][OH:29])[O:25][C:24]4=[O:30])=[CH:3][C:2]=3[F:1])=[CH:13][CH:12]=2)[N:16]=[N:17]1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 86729998HCID 86729998, compound

Product 1

HCID 178519200HCID 178519200, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude 3-(3-fluoro-4-(6-((1-(methoxymethyl)-1H-1,2,3-triazol-4-yl)amino)pyridine-3-yl)phenyl)-5-(hydroxylmethyl)oxazolidin-2-one obtained in the last step was dissolved in 20 mL tetrahydrofuran. Into the solution were added 20 mL of 6 N hydrochloric acid and 4 mL of concentrated hydrochloric acid, and reacted and refluxed for 18 h. After concentration and chromatography on a silica gel column (CH3OH:CH2Cl2=1:50), a light yellow solid was obtained. Recrystallization from methanol yielded 70 mg of 3-(4-(6-((1H-1,2,3-triazol-4-yl)amino)pyridin-3-yl)-3-fluorophenyl)-5-(hydroxylmethyl)oxazolidin-2-one, at a yield over two steps of 16.9%.

Workup

  1. customreacted
  2. temperaturerefluxed for 18 h
  3. concentrationAfter concentration and chromatography on a silica gel column (CH3OH:CH2Cl2=1:50)
  4. customa light yellow solid was obtained
  5. customRecrystallization from methanol

Sources & evidence

ORD record
ord-f2b8233260374d48ad1ebd71c4fecdfd
Source dataset
uspto-grants-2016_06
Patent number
US09359344B2

Reaction notes

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