HCID 68693588, compound → HCID 58654398, compound

HRID 1170516Notes

Reaction equation

HRID 1170516 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[S:17][N:16]=[C:15]([N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)[N:14]=1)=O)(C)(C)C>O1CCOCC1.Cl>[N:18]1([C:15]2[N:14]=[C:13]([CH:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)[S:17][N:16]=2)[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

4

Reactant 1

HCID 68693588HCID 68693588, compound

Product 1

HCID 58654398HCID 58654398, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

2-(3-Imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (359 mg, 1.01 mmol) was dissolved in dioxane (2 mL) and 6M HCl (aq) (2 mL). The reaction vessel was sealed and heated to 100° C. for 1 h. The reaction was allowed to return to room temperature while standing overnight. The reaction mixture was transferred to a separatory funnel and washed with 1M NaOH (30 mL). The aqueous layer was back extracted with DCM (50 mL). The organic layers were combined, dried over Na2SO4 to and concentrated in vacuo to afford 179 mg (80.4%) of 3-imidazol-1-yl-5-pyrrolidin-2-yl-[1,2,4]thiadiazole. [M+H]+ 221.87.

Workup

  1. customThe reaction vessel was sealed
  2. customto return to room temperature
  3. customThe reaction mixture was transferred to a separatory funnel
  4. washwashed with 1M NaOH (30 mL)
  5. extractionThe aqueous layer was back extracted with DCM (50 mL)
  6. dry with materialdried over Na2SO4 to and
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f193dc986a9459abaf4f4785da36636
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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