Sodium Iodide → 1-(1-Benzhydryl-3-azetidinyl)-5-ethyl-4-nitro-1H-pyrazole-3-carboxamide

HRID 393897Notes

Reaction equation

HRID 393897 reaction equation
[CH2:1]([C:3]1[NH:7][N:6]=[C:5]([C:8]([NH2:10])=[O:9])[C:4]=1[N+:11]([O-:13])=[O:12])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].CS(O[CH:27]1[CH2:30][N:29]([CH:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:28]1)(=O)=O>O1CCCC1.O>[CH:31]([N:29]1[CH2:30][CH:27]([N:7]2[C:3]([CH2:1][CH3:2])=[C:4]([N+:11]([O-:13])=[O:12])[C:5]([C:8]([NH2:10])=[O:9])=[N:6]2)[CH2:28]1)([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateHCID 114467375-ethyl-4-nitro-1H-pyrazole-3-carboxamide

Product 1

HCID 116471191-(1-Benzhydryl-3-azetidinyl)-5-ethyl-4-nitro-1H-pyrazole-3-carboxamideYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Ethyl-4-nitro-1H-pyrazole-3-carboxamide (WO 98/49166) (25.0 g, 136 mmol), sodium carbonate (57.6 g, 543 mmol), sodium iodide (40.7 g, 272 mmol) and 1-benzhydryl-3-azetidinyl methanesulfonate (86.2 g, 272 mmol) were suspended in tetrahydrofuran (338 mL) and water (38 mL) and heated under reflux for 5 days. The reaction mixture was then concentrated in vacuo and taken up in ethyl acetate (500 mL) and water (300 mL). The resulting precipitate was filtered, washed with ethyl acetate and water to yield the title compound as a white solid (17 g, 41.9 mmol, 31%): mp 257-260° C.; 1H NMR (400 MHz, DMSO-d6): δ=1.09 (t, 3H, J=7.6 Hz), 2.95 (q, 2H, J=7.3 Hz), 3.43 (t, 2H, J=7.6 Hz), 3.61 (t 2H, J=7.6 Hz), 4.59 (s, 1H), 5.23 (quintet, 1H, J=7.3 Hz), 7.15-7.20 (m, 2H), 7.24-7.31 (m, 4H), 7.43-7.48 (m, 4H), 7.70 (br s, 1H), 7.95 (br s, 1H); LRMS (m/z) (TSP+) 406.2 (MH+).

Workup

  1. temperatureunder reflux for 5 days
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with ethyl acetate and water

Sources & evidence

ORD record
ord-795383cb88094671aeb4051a670b2ae6
Source dataset
uspto-grants-2004_10
Patent number
US06809200B2

Reaction notes

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