Cesium carbonate → HCID 66781031, compound

HRID 1907323Notes

Reaction equation

HRID 1907323 reaction equation
[CH3:1][O:2][C:3]([C@@:5]12[CH2:14][N:13]([S:15]([C:18]3[CH:19]=[N:20][C:21](Cl)=[CH:22][CH:23]=3)(=[O:17])=[O:16])[CH2:12][CH2:11][C:10]1=[CH:9][C:8]1[N:25]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[N:26]=[CH:27][C:7]=1[CH2:6]2)=[O:4].[C:35](=O)([O-])[O-:36].[Cs+].[Cs+]>CO.O>[CH3:1][O:2][C:3]([C@@:5]12[CH2:14][N:13]([S:15]([C:18]3[CH:19]=[N:20][C:21]([O:36][CH3:35])=[CH:22][CH:23]=3)(=[O:17])=[O:16])[CH2:12][CH2:11][C:10]1=[CH:9][C:8]1[N:25]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[N:26]=[CH:27][C:7]=1[CH2:6]2)=[O:4]

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 86669987HCID 86669987, compound

Product 1

HCID 66781031HCID 66781031, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of (R)-6-(6-chloropyridine-3-sulfonyl)-1-(4-fluorophenyl)-1,4,5,6,7,8-hexahydro-1,2,6-triaza-cyclopenta[b]naphthalene-4a-carboxylic acid methyl ester (0.3 g) in methanol (10 mL) was treated with cesium carbonate (0.98 g) and water (0.5 mL) for 20 hours. The reaction mixture was diluted with water, extracted with ethyl acetate, the combined organic extracts dried over sodium sulfate and the residue concentrated under reduced pressure to provide a white foam (0.28 g). LCMS (Method G): 499.1 (M+H)+, Retention time 3.77 minutes.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe combined organic extracts dried over sodium sulfate
  3. concentrationthe residue concentrated under reduced pressure

Sources & evidence

ORD record
ord-a4972a9d64a541f28653c98b17f51648
Source dataset
uspto-grants-2013_12
Patent number
US08598154B2

Reaction notes

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