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Potassium Carbonate → HCID 70975930, compound

HRID 455280
Notes
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Reaction equation

HRID 455280 reaction equation
Br[C@H:2]1[CH2:22][N:5]2[C:6](=[O:21])[N:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:11][CH:10]=3)[CH2:8][C@H:4]2[CH2:3]1.C([O-])([O-])=O.[K+].[K+].[Cl:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[S:36]([NH2:39])(=[O:38])=[O:37]>CN(C=O)C>[Cl:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[S:36]([NH:39][C@@H:2]1[CH2:22][N:5]2[C:6](=[O:21])[N:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:11][CH:10]=3)[CH2:8][C@H:4]2[CH2:3]1)(=[O:38])=[O:37]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 814102-ChlorobenzenesulfonamideHCID 86673576HCID 86673576, compound

Product 1

HCID 70975930HCID 70975930, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (6R,7aR)-6-Bromo-2-[4-(2,2,2-trifluoro-ethoxy)-phenyl]-hexahydro-pyrrolo[1,2-c]imidazol-3-one (50 mg, 0.130 mmol) in DMF (3 mL) in a sealed tube, was added K2CO3 (27.3 mg, 0.197 mmol) and 2-Chloro-benzenesulfonamide (50.5 mg, 0.263 mmol) and heated to 80° C. for 12 h. All volatiles were removed under reduced pressure and the residue was extracted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO4 and concentrated. The residue was purified through biotage column chromatography (elution with 40% ethyl acetate in hexane) to afford 17 mg (26.5%) of the title compound as a white solid. LC-MS: 489 [M+1]+.

Workup

  1. customAll volatiles were removed under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified through biotage column chromatography (elution with 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d090ed364c6a4fe9948c161a97f5d0a7
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08497288B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes