Boron tribromide → HCID 136080883, compound

HRID 1361482Notes

Reaction equation

HRID 1361482 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:13][N:12]=[C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:21])[CH2:16][CH2:15]2)[N:10]=1.B(Br)(Br)Br>C([O-])(O)=O.[Na+]>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:13][N:12]=[C:11]([N:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:21])[CH2:18][CH2:19]2)[N:10]=1

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 58182720HCID 58182720, compound

Product 1

HCID 136080883HCID 136080883, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
-30 °C

Procedure

To isobutyl 4-(5-(2-methoxyphenyl)-1,2,4-thiadiazol-3-yl)piperazine-1-carboxylate from above was added boron tribromide solution (1 M in CH2Cl2, 1.7 mL, 1.7 mmol) at −30° C. The reaction mixture was stirred at −30° C. for 1 h and at room temperature for 3 h. To this mixture was added boron tribromide (1 M in CH2Cl2, 1.4 mL, 1.4 mmol), and the reaction was stirred for another hour. The reaction mixture was diluted with saturated NaHCO3 and extracted with CH2Cl2. The combined extracts were washed with water, dried over Na2SO4, and concentrated under reduced pressure to give a residue which was filtered and purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)) to yield isobutyl 4-(5-(2-hydroxyphenyl)-1,2,4-thiadiazol-3-yl)piperazine-1-carboxylate. LC/MS: m/z 363.3 (M+H)+ at 3.52 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. stirringthe reaction was stirred for another hour
  2. extractionextracted with CH2Cl2
  3. washThe combined extracts were washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a residue which
  7. filtrationwas filtered
  8. custompurified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

Sources & evidence

ORD record
ord-b7461a45aeb74198846416cf1973975e
Source dataset
uspto-grants-2011_02
Patent number
US07880008B2

Reaction notes

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