Hydrochloric Acid → HCID 22601342, compound

HRID 970899Notes

Reaction equation

HRID 970899 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][S:9]([C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15](O)=[O:16])(=[O:11])=[O:10].B.C1COCC1.Cl.O>C1COCC1>[OH:16][CH2:15][C:14]1[CH:13]=[C:12]([S:9]([NH:8][CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)(=[O:11])=[O:10])[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 16788272HCID 16788272, compound

Product 1

HCID 22601342HCID 22601342, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To solution of 3-[(Pyridin-2-ylmethyl)-sulfamoyl]-benzoic acid (840 mg, 2.87 mmol) in THF (5 ml) was added BH3.THF (1M, 14.4 ml, 14.4 mmol) dropwise. After the addition, the reaction mixture was allowed to stir for 18 h at room temperature, and 5 N HCl (8 ml) was carefully added, resulting in the evolution of H2. Upon heating to 70° C. for 2 h, a clear solution was obtained. Water (30 ml) was added, and the resulting solution was extracted with diethyl ether (3×20 ml). The aqueous phase was cooled to 0° C., neutralized with solid NaOH, and then solid NaHCO3 and extracted with CHCl3 (6×20 ml). The combined organic extracts were dried over MgSO4, and concentrated under reduced pressure. The crude material was used without further purification in the next reaction.

Workup

  1. additionAfter the addition
  2. customresulting in the evolution of H2
  3. temperatureUpon heating to 70° C. for 2 h
  4. customa clear solution was obtained
  5. extractionthe resulting solution was extracted with diethyl ether (3×20 ml)
  6. temperatureThe aqueous phase was cooled to 0° C.
  7. extractionsolid NaHCO3 and extracted with CHCl3 (6×20 ml)
  8. dry with materialThe combined organic extracts were dried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customThe crude material was used without further purification in the next reaction

Sources & evidence

ORD record
ord-59419663d56341ae8a8973c044e1060a
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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