Diethyl Ether → HCID 86710048, compound

HRID 1468271Notes

Reaction equation

HRID 1468271 reaction equation
[CH:1]1([S:7]([C:10]2[N:14]3[CH:15]=[CH:16][C:17]([C:19](N(CC)CC)=[O:20])=[CH:18][C:13]3=[N:12][C:11]=2[CH:26]([CH3:28])[CH3:27])(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].C([O:33]CC)C>C(O)C(C)C>[CH:1]1([S:7]([C:10]2[N:14]3[CH:15]=[CH:16][C:17]([C:19]([OH:20])=[O:33])=[CH:18][C:13]3=[N:12][C:11]=2[CH:26]([CH3:27])[CH3:28])(=[O:8])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 89954237HCID 89954237, compound

Product 1

HCID 86710048HCID 86710048, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

Compound 13 (237 mg, 0.584 mmol) was dissolved in isobutyl alcohol (1.2 mL), and the solution was stirred overnight under heat and reflux after adding a 5 mol/L sodium hydroxide aqueous solution (1.2 mL). The reaction mixture was stirred after adding diethyl ether, and the aqueous layer was removed. Then, 3 mol/L hydrochloric acid (2.0 mL) was added to the aqueous layer, and the mixture was stirred. The precipitated crystals were collected by filteration to give 3-cyclohexylsulfonyl-2-isopropylimidazo[1,2-a]pyridine-7-carboxylic acid (86.2 mg, yield 42%).

Workup

  1. temperatureunder heat
  2. temperaturereflux
  3. stirringThe reaction mixture was stirred
  4. customthe aqueous layer was removed
  5. additionThen, 3 mol/L hydrochloric acid (2.0 mL) was added to the aqueous layer
  6. stirringthe mixture was stirred
  7. customThe precipitated crystals were collected by filteration

Sources & evidence

ORD record
ord-4863227d94b64a8aa42b27fdab2fad02
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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