Sodium Carbonate → HCID 57652834, compound

HRID 2355069Notes

Reaction equation

HRID 2355069 reaction equation
Br[C:2]1[S:6][C:5]([NH2:7])=[N:4][N:3]=1.[Br:8][C:9]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:10]=1[O:11][C@H:12]1[CH2:16][CH2:15][NH:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+]>CCO>[Br:8][C:9]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:10]=1[O:11][C@H:12]1[CH2:16][CH2:15][N:14]([C:2]2[S:6][C:5]([NH2:7])=[N:4][N:3]=2)[CH2:13]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 36508832-Amino-5-bromo-1,3,4-thiadiazoleHCID 57652823HCID 57652823, compound

Product 1

HCID 57652834HCID 57652834, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromo-1,3,4-thiadiazol-2-amine (1 g, 5.6 mmol), (3S)-3-(2-bromo-5-fluorophenoxy)pyrrolidine (1.6 g, 6.1 mmol) and sodium carbonate (1.2 g, 11 mmol) in EtOH (11 mL) was degassed with nitrogen for 5 mins. The mixture was then heated at 90° C. for 3 h. The mixture was then cooled to room temperature and filtered. The solvent was evaporated and diluted with water (50 mL). The solid precipitate was filtered and washed with water followed by Et2O to afford the title product.

Workup

  1. customwas degassed with nitrogen for 5 mins
  2. temperatureThe mixture was then cooled to room temperature
  3. filtrationfiltered
  4. customThe solvent was evaporated
  5. additiondiluted with water (50 mL)
  6. filtrationThe solid precipitate was filtered
  7. washwashed with water

Sources & evidence

ORD record
ord-bbe26e9f1c414f93bedf2d243dc7a5f2
Source dataset
uspto-grants-2010_07
Patent number
US07754745B2

Reaction notes

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