Dimethylamine → HCID 66765420, compound

HRID 577280Notes

Reaction equation

HRID 577280 reaction equation
CS(O[CH2:6][C:7]1([CH2:11][N:12]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[N:13]2)[CH2:10][O:9][CH2:8]1)(=O)=O.C([O-])([O-])=O.[K+].[K+].[CH3:26][NH:27][CH3:28]>C(#N)C.C(Cl)Cl>[CH3:26][N:27]([CH3:28])[CH2:6][C:7]1([CH2:11][N:12]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[N:13]2)[CH2:10][O:9][CH2:8]1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 86671738HCID 86671738, compound

Product 1

HCID 66765420HCID 66765420, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

(3-((4-nitro-1H-pyrazol-1-yl)methyl)oxetan-3-yl)methyl methanesulfonate (0.225 g, 0.935 mmol) was suspended in acetonitrile (6 mL) with K2CO3 (0.297 g, 2.15 mmol) and dimethylamine (2M in MeOH, 1.87 mL, 3.75 mmol) in a microwave vial and sealed under Nitrogen. This was heated at 70° C. for 36 h then diluted with DCM (20 mL), washed with water (20 mL) and brine (20 mL). The organics were dried over Na2SO4, filtered and the solvent removed under vacuum. The crude product was purified by prep HPLC to give N,N-dimethyl-1-(3-((4-nitro-1H-pyrazol-1-yl)methyl)oxetan-3-yl)methanamine as a white solid (33 mg, 15% yield).

Workup

  1. customsealed under Nitrogen
  2. washwashed with water (20 mL) and brine (20 mL)
  3. dry with materialThe organics were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent removed under vacuum
  6. customThe crude product was purified by prep HPLC

Sources & evidence

ORD record
ord-620b30862c284de9998cff0d2d76c725
Source dataset
uspto-grants-2015_05
Patent number
US09040545B2

Reaction notes

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