Sodium Fluoride → N-[(5-amino-1-methyl-1H-pyrazol-4-yl)methyl]-N'-tritylethane-1,2-diamine

HRID 459651Notes

Reaction equation

HRID 459651 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[N:12]([CH3:13])[N:11]=[CH:10][C:9]=1[C:14]([NH:16][CH2:17][CH2:18][NH:19][C:20]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O.[F-].[Na+]>O1CCCC1>[NH2:7][C:8]1[N:12]([CH3:13])[N:11]=[CH:10][C:9]=1[CH2:14][NH:16][CH2:17][CH2:18][NH:19][C:20]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 5235Sodium FluorideHCID 184423955-amino-1-methyl-N-[2-(tritylamino)ethyl]-1H-pyrazole-4-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 18442411N-[(5-amino-1-methyl-1H-pyrazol-4-yl)methyl]-N'-tritylethane-1,2-diamineYield 31.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminium hydride (3.78 g) in tetrahydrofuran (150 ml) was added 5-amino-1-methyl-N-[2-(tritylamino)ethyl]-1H-pyrazole-4-carboxamide (10.64 g) at room temperature. The mixture was stirred under reflux for 18 hours. After cooling on an ice bath, to the reaction mixture were added sodium fluoride (20 g) and aqueous tetrahydrofuran solution (10 ml). The insoluble materials were removed by filtration. The resulting filtrate was concentrated in vacuo, and the residue was dissolved in chloroform. The solution was washed with 10% aqueous sodium hydroxide solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The oily residue was triturated with ethyl acetate and dried in vacuo to give N-[(5-amino-1-methyl-1H-pyrazol-4-yl)methyl]-N′-tritylethane-1,2-diamine (3.2 g) as a solid.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureAfter cooling on an ice bath, to the reaction mixture
  3. customThe insoluble materials were removed by filtration
  4. concentrationThe resulting filtrate was concentrated in vacuo
  5. dissolutionthe residue was dissolved in chloroform
  6. washThe solution was washed with 10% aqueous sodium hydroxide solution
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe oily residue was triturated with ethyl acetate
  11. customdried in vacuo

Sources & evidence

ORD record
ord-f2cb046fd81d4b088ee23a4aca2f1c53
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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