(S)-3-methoxy-1-(1-methylpyrrolidin-3-yl)-4-nitro-1H-pyrazole → (S)-3-methoxy-1-(1-methylpyrrolidin-3-yl)-1H-pyrazol-4-amine

HRID 928217Notes

Reaction equation

HRID 928217 reaction equation
[CH3:1][O:2][C:3]1[C:7]([N+:8]([O-])=O)=[CH:6][N:5]([C@H:11]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12]2)[N:4]=1>[Pd].CO>[CH3:1][O:2][C:3]1[C:7]([NH2:8])=[CH:6][N:5]([C@H:11]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12]2)[N:4]=1

Participants

4

Reactant 1

HCID 118073571(S)-3-methoxy-1-(1-methylpyrrolidin-3-yl)-4-nitro-1H-pyrazole

Product 1

HCID 118073561(S)-3-methoxy-1-(1-methylpyrrolidin-3-yl)-1H-pyrazol-4-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A nitrogen-flushed round bottom flask was charged with (S)-3-methoxy-1-(1-methylpyrrolidin-3-yl)-4-nitro-1H-pyrazole (300 mg, 1.33 mmol, 1.00 eq), 10% Pd/C (200 mg) and methanol (20 mL). The reaction mixture was sparged with hydrogen for 10 min then stirred vigorously under hydrogen atmosphere for 16 hr. The reaction mixture was then sparged with nitrogen, filtered through Celite®, and concentrated to give an oil that was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.99 (s, 1H), 4.51 (tdd, J=4.8, 7.3, 9.3 Hz, 1H), 3.74 (s, 3H), 3.36 (br. s., 2H), 2.71-2.61 (m, 2H), 2.57 (dd, J=4.8, 9.5 Hz, 1H), 2.40 (dt, J=6.5, 8.3 Hz, 1H), 2.25 (s, 3H), 2.23-2.14 (m, 1H), 1.94-1.84 (m, 1H). m/z (APCI+) for C9H17N4O 197.3 (M+H)+.

Workup

  1. customA nitrogen-flushed round bottom flask
  2. customThe reaction mixture was sparged with hydrogen for 10 min
  3. customThe reaction mixture was then sparged with nitrogen
  4. filtrationfiltered through Celite®
  5. concentrationconcentrated
  6. customto give an oil that
  7. customwas used without further purification

Sources & evidence

ORD record
ord-ee02079405684b9db75e9af6b100d351
Source dataset
uspto-grants-2016_03
Patent number
US09290496B2

Reaction notes

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