4-nitro-1H-pyrazole → HCID 67981250, compound

HRID 592398Notes

Reaction equation

HRID 592398 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[H-].[Na+].CS(O[CH:16]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17]1)(=O)=O>CN(C=O)C.CCOC(C)=O>[CH3:21][N:18]1[CH2:19][CH2:20][CH:16]([N:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]2)[CH2:17]1

Participants

6

Reactant 3

HCID 163764-nitro-1H-pyrazoleHCID 24758Sodium hydrideHCID 219142741-Methylpyrrolidin-3-yl methanesulfonate

Product 1

HCID 67981250HCID 67981250, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

4-Nitro-1H-pyrazole (0.452 g, 4.00 mmol) was dissolved in DMF (8 mL) and cooled to 0° C. NaH (0.192 g, 60% dispersion in oil, 4.80 mmol) was added and the mixture was stirred for 10 minutes. 1-Methylpyrrolidin-3-yl methanesulfonate A22 (0.717 g, 4.00 mmol) was added and the mixture was stirred for 16 hours at 100° C. The mixture was diluted with EtOAc (5 mL) and washed with sat. NH4Cl (5 mL) and water (4×5 mL). The organics were concentrated in vacuo affording a crude pale yellow oil which was purified by flash chromatography (0-30% MeOH in DCM) to give the title compound A23 as a pale yellow oil (0.575 g, 73% yield). LCMS-B: rt 1.12 min; m/z 197 [M+H]+.

Workup

  1. addition(0.717 g, 4.00 mmol) was added
  2. stirringthe mixture was stirred for 16 hours at 100° C
  3. washwashed with sat. NH4Cl (5 mL) and water (4×5 mL)
  4. concentrationThe organics were concentrated in vacuo
  5. customaffording a crude pale yellow oil which
  6. customwas purified by flash chromatography (0-30% MeOH in DCM)

Sources & evidence

ORD record
ord-646594afe54a4103bbcbb9b6e30fbb47
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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