Hydrochloric Acid → HCID 86636679, compound

HRID 2075407Notes

Reaction equation

HRID 2075407 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:32][C:33]1[CH:34]=[N:35][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:37][CH:38]=1)[CH2:10][CH2:11][C:12]1[S:16][C:15]([C:17]2[CH:18]=[CH:19][C:20]([N+:29]([O-])=O)=[C:21]([CH2:23][C:24](OCC)=[O:25])[CH:22]=2)=[N:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C([O-])(O)=O.[Na+]>CCO.O.[Fe]>[O:25]=[C:24]1[CH2:23][C:21]2[C:20](=[CH:19][CH:18]=[C:17]([C:15]3[S:16][C:12]([CH2:11][CH2:10][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:32][C:33]4[CH:34]=[N:35][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:37][CH:38]=4)=[N:13][N:14]=3)[CH:22]=2)[NH:29]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 57991946HCID 57991946, compound

Product 1

HCID 86636679HCID 86636679, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Iron powder (48 mg, 853 μmol) was added to a suspension of ethyl 2-(5-(5-((R)-3-(tert-butoxycarbonylamino)-4-(6-(trifluoromethyl)pyridin-3-yl)butyl)-1,3,4-thiadiazol-2-yl)-2-nitrophenyl)acetate (104 mg, 171 μmol) in EtOH (1.5 mL). 2N aqueous HCl (256 μL, 512 μmol) was added, and the mixture was heated under reflux for 4 hours. Saturated aqueous NaHCO3 (5 mL) was added dropwise and the mixture was stirred at room temperature for 5 minutes. It was diluted with H2O (5 mL) and extracted with DCM (3×15 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resulting light yellow oil was absorbed onto silica gel and purified by flash chromatography (silica gel, 2% to 6% MeOH/DCM) to deliver tert-butyl (R)-4-(5-(2-oxoindolin-5-yl)-1,3,4-thiadiazol-2-yl)-1-(6-(trifluoromethyl)pyridin-3-yl)butan-2-ylcarbamate (49 mg, 54%) as a white solid. LCMS (API-ES) m/z: 534.0 (M+H+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. extractionextracted with DCM (3×15 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting light yellow oil was absorbed onto silica gel
  7. custompurified by flash chromatography (silica gel, 2% to 6% MeOH/DCM)

Sources & evidence

ORD record
ord-16021fffe55549b9b9a92553fb71564b
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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