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Potassium Carbonate → HCID 68523343, compound

HRID 1992351
Notes
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Reaction equation

HRID 1992351 reaction equation
Br[CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[C:15]([O:19][C:20]([N:22]1[CH2:29][CH:28]2[O:30][CH:24]([CH2:25][NH:26][CH2:27]2)[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:15]([O:19][C:20]([N:22]1[CH2:23][CH:24]2[O:30][CH:28]([CH2:27][N:26]([CH2:2][CH2:3][NH:4][S:5]([C:8]3[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=3)(=[O:7])=[O:6])[CH2:25]2)[CH2:29]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2779738N-(2-bromoethyl)-4-fluorobenzenesulfonamideHCID 185404123-Boc-9-oxa-3,7-diazabicyclo[3.3.1]nonane

Product 1

HCID 68523343HCID 68523343, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of N-(2-Bromo-ethyl)-4-fluoro-benzenesulfonamide (7 g, 0.0179 mol; see step (i) above) and 9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (11.2 g, 0.159 mol; see WO 01/28992) and K2CO3 (9.7 g, 0.0798 mol) in dry acetonitrile (70 ml) was stirred at 60° C. overnight under nitrogen atmosphere. The reaction mixture was partitioned between brine and ethyl acetate. Organic layer was washed with brine and dried over sodium sulfate. Solvent evaporation under reduced pressure followed by column chromatography over silica gel using 7% ethyl acetate in petroleum ether as eluent afforded the sub-title compound as a solid. Yield: 4 g

Workup

  1. customThe reaction mixture was partitioned between brine and ethyl acetate
  2. washOrganic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customSolvent evaporation under reduced pressure

Sources & evidence

ORD record
ord-0dd497de678b4d41a180dc8c20451ba6
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07648985B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes