Hydrochloric Acid → HCID 178526038, compound

HRID 1045096Notes

Reaction equation

HRID 1045096 reaction equation
Br[CH2:2][C:3]([OH:5])=[O:4].[Cl:6][C:7]1[C:16]([C:17]#[C:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][C:10]2[NH:11][C:12](=[S:14])[NH:13][C:9]=2[CH:8]=1.[OH-].[K+].Cl>CCO.O>[Cl:6][C:7]1[C:16]([C:17]#[C:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][C:10]2[N:11]=[C:12]([S:14][CH2:2][C:3]([OH:5])=[O:4])[NH:13][C:9]=2[CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6227Bromoacetic AcidHCID 14797Potassium HydroxideHCID 86762102HCID 86762102, compound

Product 1

HCID 178526038HCID 178526038, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of bromoacetic acid (47.8 mg, 0.344 mmol) in EtOH (1 mL) was added dropwise to a 20 mL scintillation vial equipped with a stirring bar and a septum cap containing a solution of compound 1-3 (49.0 mg, 0.172 mmol) in EtOH (1 mL). To this solution, 1M KOH (2 mL) was added dropwise, and the resulting mixture was stirred at rt for 1 h. The reaction mixture was then diluted with water (4 mL) and acidified with 10% aqueous HCl. The solution was extracted with EtOAc (3 mL then twice 1 mL), extracts were combined and evaporated to dryness in vacuo. The resulting oily residue was dissolved in DMSO (1.0 mL), filtered and purified by reverse-phase HPLC to give the title compound as white solid. LR-MS (API-ES): calculated for C17H11ClN2O2S 342.0, observed m/e 343.1 (M+H)+ (Rt 7.71 min).

Workup

  1. customvial equipped with a stirring bar
  2. customa septum cap
  3. extractionThe solution was extracted with EtOAc (3 mL
  4. customevaporated to dryness in vacuo
  5. dissolutionThe resulting oily residue was dissolved in DMSO (1.0 mL)
  6. filtrationfiltered
  7. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-a0a4f4a854834a28923d43e04c0bf4ca
Source dataset
uspto-grants-2013_10
Patent number
US08563746B2

Reaction notes

Loading…