Sodium Bicarbonate → HCID 178448150, compound

HRID 539032Notes

Reaction equation

HRID 539032 reaction equation
[CH:1]([C@@H:4]1[N:8]([C:9]2[CH:14]=[CH:13][N:12]3[N:15]=[CH:16][C:17]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5[N:28]=[CH:27][N:26](COCC[Si](C)(C)C)[N:25]=5)=[CH:20][CH:19]=4)=[C:11]3[N:10]=2)[C:7](=[O:37])[NH:6][CH2:5]1)([CH3:3])[CH3:2].C([O-])(O)=O.[Na+]>CCO>[NH:26]1[CH:27]=[N:28][C:24]([C:21]2[CH:20]=[CH:19][C:18]([C:17]3[CH:16]=[N:15][N:12]4[CH:13]=[CH:14][C:9]([N:8]5[C@@H:4]([CH:1]([CH3:2])[CH3:3])[CH2:5][NH:6][C:7]5=[O:37])=[N:10][C:11]=34)=[CH:23][CH:22]=2)=[N:25]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67033259(S)-5-isopropyl-1-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one

Product 1

HCID 178448150HCID 178448150, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (S)-5-isopropyl-1-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one (Example 25, Step 4, 12 mg, 0.023 mmol) and EtOH/6N aqueous HCl (1:2, 0.5 mL total) was heated at reflux for 3 hours. After cooling, the reaction mixture was neutralized by slow addition of saturated aqueous NaHCO3 solution. The mixture was extracted with dichloromethane, and the combined extracts were washed with brine, dried and concentrated. The residue was purified by column chromatography (12% MeOH in dichloromethane) to give (S)-1-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-5-isopropylimidazolidin-2-one (6 mg, 67%) as a pale yellow solid. LCMS (APCI+) m/z 389 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling
  4. extractionThe mixture was extracted with dichloromethane
  5. washthe combined extracts were washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (12% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-ea3b1376814a4dee9ff25f0e48e418c2
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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