Dimethylformamide → HCID 68284326, compound

HRID 571608Notes

Reaction equation

HRID 571608 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:32])[N:14]([CH3:31])[N:15]=[C:16]([O:26][CH2:27][C:28](O)=[O:29])[C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:2].S(Cl)(Cl)=O.C[N:38](C=O)C>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:32])[N:14]([CH3:31])[N:15]=[C:16]([O:26][CH2:27][C:28](=[O:29])[NH2:38])[C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 86699519HCID 86699519, compound

Product 1

HCID 68284326HCID 68284326, compoundYield 839.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (4-(2,6-diethyl-4-methylphenyl)-5-benzyloxy-2-methyl-3(2H)-pyridazinone-6-yl)oxyacetic acid (530 mg, 1.53 mmol), thionyl chloride (290 mg, 2.43 mmol) and DMF (10 mg) in toluene (15 ml) was stirred at 50° C. for 45 minutes. The reaction solution was cooled to room temperature, and then concentrated under reduced pressure. The residue was dissolved in THF (5 ml), and aqueous ammonia (2 ml) was slowly added under ice-cooling. After the reaction solution was stirred at room temperature for 30 minutes, the reaction solution was diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and concentrated under reduced pressure to give 500 mg of Compound (I-35-1) (yield: 94%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in THF (5 ml)
  3. additionaqueous ammonia (2 ml) was slowly added under ice-
  4. temperaturecooling
  5. additionthe reaction solution was diluted with water
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a9c23e8f2ee44089b70ff354ce2b28fb
Source dataset
uspto-grants-2015_05
Patent number
US09029295B2

Reaction notes

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