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Potassium Carbonate → 9-(8-aza-bicyclo[3.2.1]oct-3-ylidene)-5-methoxy-9H-xanthene-3-carboxylic acid diethylamide

HRID 733397
Notes
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Reaction equation

HRID 733397 reaction equation
[CH2:1]([N:3]([CH2:36][CH3:37])[C:4]([C:6]1[CH:7]=[CH:8][C:9]2[C:10](=[C:22]3[CH2:28][CH:27]4[N:29](C(=O)C(F)(F)F)[CH:24]([CH2:25][CH2:26]4)[CH2:23]3)[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[C:15]([O:20][CH3:21])[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:36]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[CH:8][C:9]2[C:10](=[C:22]3[CH2:23][CH:24]4[NH:29][CH:27]([CH2:26][CH2:25]4)[CH2:28]3)[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[C:15]([O:20][CH3:21])[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 578392625-Methoxy-9-[8-(2,2,2-trifluoro-acetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthene-3-carboxylic acid diethylamide2×

Product 1

HCID 111775769-(8-aza-bicyclo[3.2.1]oct-3-ylidene)-5-methoxy-9H-xanthene-3-carboxylic acid diethylamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-methoxy-9-[8-(2,2,2-trifluoro-acetyl)-8-aza-bicyclo[3.2.1]-oct-3ylidene]-9H-xanthene-3-carboxylic acid diethylamide, 5c (3.2g, 6.22 mmol) and potassium carbonate (1.89 g, 13.7 mmol) in methanol (50 mL) was stirred at rt overnight. The mixture was evaporated, and partitioned between methylene chloride (100 mL) and water (100 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated, yielding 2.72 g of 9-(8-aza-bicyclo[3.2.1]oct-3-ylidene)-5-methoxy-9H-xanthene-3-carboxylic acid diethylamide, 6c. MS m/z=419.0 (MH+).

Workup

  1. customThe mixture was evaporated
  2. custompartitioned between methylene chloride (100 mL) and water (100 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-a14745aed8454bb4bbbffd096d72d657
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07589104B2

Reaction notes

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