Ammonia → 5-Amino-1-(oxan-4-yl)-1H-pyrazole-4-carboxamide

HRID 2424783Notes

Reaction equation

HRID 2424783 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[N:5]=[CH:4][C:3]=1[C:13]#[N:14].[OH:15]O.N>C(O)C>[NH2:1][C:2]1[N:6]([CH:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[N:5]=[CH:4][C:3]=1[C:13]([NH2:14])=[O:15]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 426091305-Amino-1-(oxan-4-yl)-1H-pyrazole-4-carbonitrile

Product 1

HCID 426091315-Amino-1-(oxan-4-yl)-1H-pyrazole-4-carboxamideYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 5-amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carbonitrile (˜228 mmol) in ethanol (300 mL) was treated with 35% aqueous H2O2 (100 mL) followed by aqueous ammonia (300 mL). The reaction mixture was stirred for 48 h at ambient temp and then quenched with aq saturated sodium thiosulfate (800 mL) and concentrated under reduced pressure to remove most of the ethanol. The resulting solid was removed by filtration and washed with water (2×200 mL) and ether (2×150 mL). The solid was dried in vacuo to constant weight (31 g, 65% yield for 2 steps). 400 MHz 1H NMR (CD3OD) δ 7.67 (s, 1H), 4.27-4.21 (m, 1H), 4.03 (dd, J=11.6, 4.6 Hz, 2H), 3.28 (t, J=1.7 Hz, 2H), 2.14-2.04 (m, 2H), 1.81-1.78 (m, 2H). MS: (M1H m/z=382.2).

Workup

  1. customquenched with aq saturated sodium thiosulfate (800 mL)
  2. concentrationconcentrated under reduced pressure
  3. customto remove most of the ethanol
  4. customThe resulting solid was removed by filtration
  5. washwashed with water (2×200 mL) and ether (2×150 mL)
  6. customThe solid was dried in vacuo to constant weight (31 g, 65% yield for 2 steps)

Sources & evidence

ORD record
ord-9fbe75d68b594f1794f9d2642cbfc22f
Source dataset
uspto-grants-2011_06
Patent number
US07964607B2

Reaction notes

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