Triethylamine → HCID 57897982, compound

HRID 1693556Notes

Reaction equation

HRID 1693556 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[C:15]([C:24](O)=[O:25])=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:27]2[CH:32]=[CH:31][C:30]([CH:33]([CH3:35])[CH3:34])=[CH:29][CH:28]=2)=[CH:4][CH:3]=1.O=S(Cl)Cl.O[NH:41][C:42](=[NH:44])[CH3:43].CCN(CC)CC>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13](=[O:14])[C:12]3[C:15]([C:24]4[O:25][N:44]=[C:42]([CH3:43])[N:41]=4)=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:27]2[CH:32]=[CH:31][C:30]([CH:33]([CH3:34])[CH3:35])=[CH:29][CH:28]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 67282062HCID 67282062, compoundHCID 178465666HCID 178465666, compound

Product 1

HCID 57897982HCID 57897982, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(4-Chloro-phenyl)-6-(4-isopropyl-phenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid (15 mg, 0.031 mmol) is treated with SOCl2 (0.5 mL) at 80° C. for 1 h. and cooled down to room temperature. SOCl2 is removed under vacuum and the residue is dissolved in anhydrous dichloromethane (0.5 mL). N-hydroxy-acetamidine (9 mg, 0.12 mmol) is added followed by Et3N (0.02 mL). The mixture is stirred at room temperature for 1 h and then poured into water (5 mL). The mixture is extracted with EtOAc(3×3 mL). After the combined extracts is concentrated and dried under vacuum for 5 h., the residue is dissolved in anhydrous dioxane (0.5 mL) followed by the addition of NaOAc (15 mg). The mixture is stirred at 80° C. for 24 h to complete the conversion. After cooling down to room temperature, the mixture is treated with water and extracted with EtOAc. The combined extracts is concentrated and the residue is purified by preparative LC/MS to provide the title compound 5-(4-Chloro-phenyl)-6-(4-isopropyl-phenyl)-3-(3-methyl-[1,2,4]oxadiazol-5-yl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one. 1H NMR (CDCl3) δ (ppm) 8.21(d, 2H), 7.54(t, 2H), 7.42(t, 1H), 7.32 (d, 2H), 7.29(d, 2H), 7.12(m, 4H), 2.87(m, 1H), 2.55(s, 3H), 1.20(d, 6H). HPLC-MS calculated C29H23ClN6O2 (M+1+): 523.2. Found: 523.2.

Workup

  1. customSOCl2 is removed under vacuum
  2. dissolutionthe residue is dissolved in anhydrous dichloromethane (0.5 mL)
  3. extractionThe mixture is extracted with EtOAc(3×3 mL)
  4. concentrationAfter the combined extracts is concentrated
  5. customdried under vacuum for 5 h.
  6. dissolutionthe residue is dissolved in anhydrous dioxane (0.5 mL)
  7. additionfollowed by the addition of NaOAc (15 mg)
  8. stirringThe mixture is stirred at 80° C. for 24 h
  9. temperatureAfter cooling down to room temperature
  10. additionthe mixture is treated with water
  11. extractionextracted with EtOAc
  12. concentrationThe combined extracts is concentrated
  13. customthe residue is purified by preparative LC/MS

Sources & evidence

ORD record
ord-a6746e6ae9a24d648c1c6e4b54898b37
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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