Dimethylamine → HCID 67296750, compound

HRID 1807216Notes

Reaction equation

HRID 1807216 reaction equation
[CH3:1][C:2]([O:13][CH2:14][C@@H:15]1[CH2:17][O:16]1)([CH3:12])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[N:5]1.[CH3:18][NH:19][CH3:20]>C(O)(C)C>[CH3:18][N:19]([CH3:20])[CH2:17][C@H:15]([OH:16])[CH2:14][O:13][C:2]([CH3:12])([CH3:1])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[N:5]1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 59249334HCID 59249334, compound

Product 1

HCID 67296750HCID 67296750, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Compound (S)-1-dimethylamino-3-[1,1-dimethyl-2-(3-nitro-pyrazol-1-yl)-ethoxy]-propan-2-ol was prepared by reacting 1-[2-methyl-2-((S)-1-oxiranylmethoxy)-propyl]-3-nitro-1H-pyrazole (0.39 g, 1.62 mmol), isopropyl alcohol (6 mL), and dimethylamine (3 mL, 6 mmol, 2 M in dioxane) under microwave conditions at 130° C. for 15 min. The mixture was extracted with dichloromethane and water. The organic layer was separated and the solvent evaporated under reduced pressure to yield (S)-1-dimethylamino-3-[1,1-dimethyl-2-(3-nitro-pyrazol-1-yl)-ethoxy]-propan-2-ol (0.4 g, 87%). This compound was reduced under the following conditions. The mixture of (S)-1-dimethylamino-3-[1,1-dimethyl-2-(3-nitro-pyrazol-1-yl)-ethoxy]-propan-2-ol (0.39 g, 1.66 mmol), ethyl acetate (30 mL), ethanol (30 mL) was added to a Parr bottle with 10% Pd/C (0.22 g) and subjected hydrogen gas (20 psi) for 2 h under the Parr Shaker Apparatus conditions. Work up by filtration via a glass membrane filter paper, solvent was removed under reduced pressure to afford (S)-1-[2-(3-amino-pyrazol-1-yl)-1,1-dimethyl-ethoxy]-3-dimethylamino-propan-2-ol as an oil (0.37 g, 97.5%).

Workup

  1. customCompound (S)-1-dimethylamino-3-[1,1-dimethyl-2-(3-nitro-pyrazol-1-yl)-ethoxy]-propan-2-ol was prepared
  2. customat 130° C.
  3. customfor 15 min
  4. extractionThe mixture was extracted with dichloromethane and water
  5. customThe organic layer was separated
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-a27f2f510a284c6394bf51756e35f3ac
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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