2-Amino-2-methyl-1-propanol → HCID 18738349, compound

HRID 1934367Notes

Reaction equation

HRID 1934367 reaction equation
C(Cl)(=O)C(Cl)=O.[NH:7]1[CH:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[N:8]1.[NH2:15][C:16]([CH3:20])([CH3:19])[CH2:17][OH:18].C([O-])(O)=O.[Na+]>CN(C=O)C.C(Cl)Cl>[OH:18][CH2:17][C:16]([NH:15][C:12]([C:10]1[CH:9]=[N:8][NH:7][CH:11]=1)=[O:14])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 118072-Amino-2-methyl-1-propanolHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 3015937Pyrazole-4-carboxylic acid

Product 1

HCID 18738349HCID 18738349, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of DMF (2 drops) and oxalyl chloride (0.88 g, 4.5 mmol) in methylene chloride (4 ml) was added to a suspension of 4-pyrazolecarboxylic acid (0.50 g, 4.5 mmol) in methylene chloride (6 ml) and stirred at room temperature for 1 hour. The reaction mixture was concentrated and dried under a reduced pressure. To a suspension of the obtained solid in methylene chloride (5 ml) cooled in an ice-bath, 2-amino-2-methyl-1-propanol (1.33 g, 15 mmol) was added. The mixture was stirred at room temperature for 1 hour, added saturated aqueous NaHCO3 to, and concentrated and dried under a reduced pressure. The residue was extracted with warm chloroform and the solvent was evaporated under a reduced pressure. The residue was subjected to silica gel chromatography (chloroform/methanol/triethylamine=100/10/1) to give the title compound (0.37 g, 45%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdried under a reduced pressure
  3. additionTo a suspension of the obtained solid in methylene chloride (5 ml)
  4. temperaturecooled in an ice-bath
  5. stirringThe mixture was stirred at room temperature for 1 hour
  6. concentrationconcentrated
  7. customdried under a reduced pressure
  8. extractionThe residue was extracted with warm chloroform
  9. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-bdba3839a4314dad8fbe5838e72fa2f1
Source dataset
uspto-grants-2002_05
Patent number
US06384033B1

Reaction notes

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