Hydrochloric Acid → HCID 46190896, compound

HRID 1045099Notes

Reaction equation

HRID 1045099 reaction equation
Br[CH2:2][C:3]([OH:5])=[O:4].[C:6]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:11]=[CH:10][C:9]([C:12]2[C:21]([Cl:22])=[CH:20][C:15]3[NH:16][C:17](=[S:19])[NH:18][C:14]=3[CH:13]=2)=[CH:8][CH:7]=1.[OH-].[K+].Cl>CCO.O>[C:6]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:11]=[CH:10][C:9]([C:12]2[C:21]([Cl:22])=[CH:20][C:15]3[NH:16][C:17]([S:19][CH2:2][C:3]([OH:5])=[O:4])=[N:18][C:14]=3[CH:13]=2)=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6227Bromoacetic AcidHCID 14797Potassium HydroxideHCID 86762103HCID 86762103, compound

Product 1

HCID 46190896HCID 46190896, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of bromoacetic acid (43.4 mg, 0.312 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 2-3 (52.6 mg, 0.156 mmol) in EtOH (0.5 mL). To this solution, 1M KOH (1.5 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 three times 1 mL). Extracts were combined and evaporated to dryness in vacuo. The resulting oily residue was dissolved in DMSO (1 mL), filtered and purified by reverse-phase HPLC with to give the title compound as white solid. 1H NMR (DMSO-d6, 400 MHz) δ 7.70-7.76 (4H, m), 7.64 (1H, s), 7.46-7.55 (4H, m), 7.45 (1H, s), 7.36-7.40 (1H, m), 4.12 (2H, s); LRMS (API-ES): calculated for C21H15ClN2O2S 394.1, observed m/e 395.0 (M+H)+ (Rt 3.14 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 mL)
  6. filtrationfiltered
  7. custompurified by reverse-phase HPLC with

Sources & evidence

ORD record
ord-47e78eb02d3b4716979e70d081b2a42b
Source dataset
uspto-grants-2013_10
Patent number
US08563746B2

Reaction notes

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