Citric Acid → HCID 117700524, compound

HRID 873537Notes

Reaction equation

HRID 873537 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:13]([C:15]1[C:16]([C:50](O)=[O:51])=[N:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([CH:29]3[C:42]4[C:41](=[O:43])[CH2:40][C:39]([CH3:45])([CH3:44])[CH2:38][C:37]=4[O:36][C:35]4[CH2:34][C:33]([CH3:47])([CH3:46])[CH2:32][C:31](=[O:48])[C:30]3=4)[C:22]=2[CH3:49])=[CH:19][CH:20]=1)[CH3:14].[CH3:53][S:54]([NH2:57])(=[O:56])=[O:55].N12CCCN=C1CCCCC2.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[CH2:13]([C:15]1[C:16]([C:50]([NH:57][S:54]([CH3:53])(=[O:56])=[O:55])=[O:51])=[N:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([CH:29]3[C:30]4[C:31](=[O:48])[CH2:32][C:33]([CH3:47])([CH3:46])[CH2:34][C:35]=4[O:36][C:37]4[CH2:38][C:39]([CH3:45])([CH3:44])[CH2:40][C:41](=[O:43])[C:42]3=4)[C:22]=2[CH3:49])=[CH:19][CH:20]=1)[CH3:14]

Participants

7

Reactant 5

HCID 311Citric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 78324914HCID 78324914, compound

Product 1

HCID 117700524HCID 117700524, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,1′-Carbonyldiimidazole (104 mg, 0.64 mmol) was added to a solution of the 3-ethyl-6-[4-methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carboxylic acid produced in Example 13 (267 mg, 0.49 mmol) in DMF (5.3 ml) at room temperature, and the mixture thus obtained was then stirred at the same temperature as above for 1.5 hours. Thereafter, methanesulfonamide (60.7 mg, 0.64 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.096 ml, 0.64 mmol) were added to the resulting solution at room temperature, and the mixture thus obtained was then stirred at the same temperature as above for 3 hours. Thereafter, an aqueous solution of citric acid (472 mg, 2.46 mmol) was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. The organic layer thus obtained was washed with water, and was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the residue thus obtained was then purified by silica gel column chromatography (methanol:dichloromethane=0:1 to 1:9, v/v). The solid thus obtained was washed with diethyl ether, followed by collection by filtration and drying, to obtain the title compound (128 mg, yield: 42%).

Workup

  1. customthe mixture thus obtained
  2. customthe mixture thus obtained
  3. stirringwas then stirred at the same temperature as above for 3 hours
  4. extractionthe mixed solution was then extracted with ethyl acetate
  5. customThe organic layer thus obtained
  6. washwas washed with water
  7. dry with materialwas then dried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled away under reduced pressure
  9. customthe residue thus obtained
  10. customwas then purified by silica gel column chromatography (methanol:dichloromethane=0:1 to 1:9, v/v)
  11. customThe solid thus obtained
  12. washwas washed with diethyl ether
  13. filtrationfollowed by collection by filtration
  14. customdrying

Sources & evidence

ORD record
ord-324fe58ac9374e2db94895af2432c695
Source dataset
uspto-grants-2015_03
Patent number
US08975263B2

Reaction notes

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