Water → (R)-1-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-3-amine

HRID 1051201Notes

Reaction equation

HRID 1051201 reaction equation
[CH3:1][C:2]1([CH3:22])[O:6][C@H:5]([CH2:7][N:8]2[CH:12]=[CH:11][C:10]([NH:13]C(=O)C3C=CC=CC=3)=[N:9]2)[CH2:4][O:3]1.O.[OH-].[Na+]>CO>[CH3:1][C:2]1([CH3:22])[O:6][C@H:5]([CH2:7][N:8]2[CH:12]=[CH:11][C:10]([NH2:13])=[N:9]2)[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 90258685HCID 90258685, compound

Product 1

HCID 59344941(R)-1-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-3-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-yl]-benzamide (150 mg, 0.5 mmol) was dissolved in methanol (2 ml), and water (1 ml) was added in one portion. The mixture was stirred at room temperature for 30 minutes. NaOH (120 mg, 3 mmol) was added. The mixture was stirred at reflux for 18 h. UPLC indicated the conversion was ˜20%, so the mixture was agitated for another 20 h. The conversation was still ˜40%. Another portion of NaOH (120 mg, 3 mmol) was added into the mixture. The mixture was agitated at reflux for another 20 h. The conversation was ˜70%. No further workup.

Workup

  1. stirringThe mixture was stirred
  2. temperatureat reflux for 18 h
  3. stirringso the mixture was agitated for another 20 h
  4. stirringThe mixture was agitated
  5. temperatureat reflux for another 20 h

Sources & evidence

ORD record
ord-d0836a60285048a0855b8d755537d0f0
Source dataset
uspto-grants-2016_07
Patent number
US09388168B2

Reaction notes

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