Hydrochloric Acid → HCID 57500565, compound

HRID 1393691Notes

Reaction equation

HRID 1393691 reaction equation
[CH3:1][C:2]1[CH:13]=[C:5]2[N:6]=[CH:7][C:8]([C:10]([OH:12])=O)=[CH:9][N:4]2[N:3]=1.C(Cl)(=O)C(Cl)=O.[NH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][NH2:23].Cl>ClCCl.CN(C)C=O.O.C(N(CC)CC)C>[NH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][NH:23][C:10]([C:8]1[CH:7]=[N:6][C:5]2[N:4]([N:3]=[C:2]([CH3:1])[CH:13]=2)[CH:9]=1)=[O:12]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 131282-MethylpropylenediamineHCID 65578Oxalyl chlorideHCID 230919472-Methylpyrazolo(1,5-a)pyrimidine-6-carboxylic acid

Product 1

HCID 57500565HCID 57500565, compoundYield 56%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

2-Methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid (0.18 g) was suspended in dichloromethane (5 ml), and N,N-dimethylformamide (1 drop) was added thereto. The mixture was cooled to 0° C., and a solution of oxalyl chloride (10 μl) in dichloromethane (3 ml) was added dropwise thereto over 10 minutes, and the mixture was stirred as such for 1 hour at 0° C. Thereafter, the mixture was stirred for 5 hours at room temperature to prepare the corresponding acid chloride. 2-Amino-2-methylpropylamine (0.11 g) was dissolved in dichloromethane, and triethylamine (0.33 ml) was added thereto and cooled to −78° C. The prepared acid chloride solution was added dropwise thereto over 30 minutes and stirred as such for 30 minutes. The temperature of the mixture was increased to room temperature, and the mixture was stirred for 1 hour at room temperature. Water was added thereto, and the aqueous phase was acidified by 2 N hydrochloric acid. After washing with chloroform, the aqueous phase was alkalinized by 5 N sodium hydroxide solution and extracted with chloroform. The organic phase was washed with a saturated saline solution and dried over sodium sulfate anhydrous. The product was concentrated under reduced pressure to give the title compound (0.14 g, Y.:56%) as yellow crystals.

Workup

  1. stirringThereafter, the mixture was stirred for 5 hours at room temperature
  2. temperaturecooled to −78° C
  3. waitover 30 minutes
  4. stirringstirred as such for 30 minutes
  5. temperatureThe temperature of the mixture was increased to room temperature
  6. stirringthe mixture was stirred for 1 hour at room temperature
  7. washAfter washing with chloroform
  8. extractionextracted with chloroform
  9. washThe organic phase was washed with a saturated saline solution
  10. dry with materialdried over sodium sulfate anhydrous
  11. concentrationThe product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7495c0be91f046fbb0d3d46827de5f14
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

Loading…