Hydrochloric Acid → HCID 90033544, compound

HRID 872994Notes

Reaction equation

HRID 872994 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][N:4]=1.CC[N:12]([CH2:15][CH3:16])[CH2:13][CH3:14].CN1C(C)=[C:21]([C:24](O)=[O:25])[C:20](=[O:27])[N:19]1[C:28]1C=CC=CC=1.[CH:34]1[CH:39]=NC2N(O)N=N[C:36]=2[CH:35]=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.O>[OH:9][C:6]1[CH:7]=[CH:8][C:3]([NH:2][C:24]([C:21]2[C:20](=[O:27])[N:19]([CH3:28])[N:12]([C:13]3[CH:14]=[CH:36][CH:35]=[CH:34][CH:39]=3)[C:15]=2[CH3:16])=[O:25])=[N:4][CH:5]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 246564Antipyric acidHCID 457908886-Aminopyridin-3-ol--hydrogen chloride (1/1)

Product 1

HCID 90033544HCID 90033544, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 2-amino-5-hydroxypyridine hydrochloride (500 mg, 3.41 mmol) and Et3N (0.77 mL, 5.5 mmol) in DMF (8 mL) was stirred at rt for 1 hour. At the same time, to a solution of 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (0.64 g, 2.75 mmol), HOAT (449 mg, 3.3 mmol) and EDCI (0.63 g, 3.3 mmol) in DMF (8 mL) was added Et3N (0.77 mL, 5.5 mmol) drop wise. The mixture was stirred at rt for 1 hour, followed by the addition of the above prepared mixture. The reaction was heated at 60° C. for 5 hours, then cooled to rt and diluted with water (150 mL). and adjust to pH=6 with HCl (1 M). The mixture was extracted with EtOAc (20 mL×4), and the combined organic phases were washed with brine (20 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (v/v)=10/1) to give the title compound as a pale yellow solid (699 mg, 78%).

Workup

  1. stirringThe mixture was stirred at rt for 1 hour
  2. additionfollowed by the addition of the above prepared mixture
  3. temperatureThe reaction was heated at 60° C. for 5 hours
  4. temperaturecooled to rt
  5. extractionThe mixture was extracted with EtOAc (20 mL×4)
  6. washthe combined organic phases were washed with brine (20 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by a silica gel column chromatography (DCM/MeOH (v/v)=10/1)

Sources & evidence

ORD record
ord-34ad6a56232a4ae68cf3c68c1ee155f2
Source dataset
uspto-grants-2015_03
Patent number
US08975282B2

Reaction notes

Loading…