Citric Acid → HCID 58453106, compound

HRID 1422518Notes

Reaction equation

HRID 1422518 reaction equation
[H-].[Na+].[CH:3]1([C:6](=[O:10])[CH2:7][C:8]#[N:9])[CH2:5][CH2:4]1.[CH3:11][C:12]1[N:20]=[C:19]([N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)[CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH:3]1([C:6](=[O:10])[CH:7]([C:14]([C:13]2[C:12]([CH3:11])=[N:20][C:19]([N:21]3[CH:25]=[N:24][CH:23]=[N:22]3)=[CH:18][CH:17]=2)=[O:15])[C:8]#[N:9])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 98127633-Cyclopropyl-3-oxopropanenitrileHCID 584530902-methyl-6-(1H-1,2,4-triazol-1-yl)nicotinic acid chloride

Product 1

HCID 58453106HCID 58453106, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A THF (2 ml) suspension of sodium hydride (0.06 g, 60% oil suspension, 18.78 mmol) was cooled in an ice bath, and a THF (2 ml) solution of 3-cyclopropyl-3-oxopropanenitrile was dripped thereto. To the obtained reaction solution, a THF (3 ml) solution of 2-methyl-6-(1H-1,2,4-triazol-1-yl)nicotinic acid chloride (0.16 g, 0.73 mmol) was dripped. The resultant was stirred at room temperature for 3 hours. The obtained reaction solution was made acidic with a citric acid aqueous solution, and the product was extracted with ethyl acetate. The obtained organic layer was washed with water, dried with magnesium sulfate and concentrated to obtain the desired product (0.14 g, yield 64%).

Workup

  1. temperaturewas cooled in an ice bath
  2. customTo the obtained reaction solution
  3. customThe obtained reaction solution
  4. extractionthe product was extracted with ethyl acetate
  5. washThe obtained organic layer was washed with water
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c120433afb5e4c8eaa5b4d6d03b5e644
Source dataset
uspto-grants-2015_01
Patent number
US08927458B2

Reaction notes

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