Water → HCID 17962014, compound

HRID 349577Notes

Reaction equation

HRID 349577 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:9]1[CH:10]=[N:11][N:12]([CH2:34][C:35]([NH2:37])=O)[C:13]=1[NH:14][C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)#[N:8].[F-].[Na+].O>O1CCCC1>[NH2:37][CH2:35][CH2:34][N:12]1[C:13]([NH:14][C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]([CH2:7][NH2:8])[CH:10]=[N:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 5235Sodium FluorideHCID 17961968HCID 17961968, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 17962014HCID 17962014, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (3.73 g) in tetrahydrofuran (100 ml) was added 2-[4-cyano-5-(tritylamino)-1H-pyrazol-1-yl]acetamide (5 g) at room temperature. The mixture was refluxed for 23 hours. After cooling on an ice bath, sodium fluoride (16.5 g) and water (7.1 ml) were added to the reaction mixture. The insoluble materials were removed by filtration. The filtrate was evaporated in vacuo and triturated with diisopropyl ether to give 1-(2-aminoethyl)-4-(aminomethyl)-5-tritylaminopyrazole (2.17 g).

Workup

  1. temperatureThe mixture was refluxed for 23 hours
  2. temperatureAfter cooling on an ice bath
  3. customThe insoluble materials were removed by filtration
  4. customThe filtrate was evaporated in vacuo
  5. customtriturated with diisopropyl ether

Sources & evidence

ORD record
ord-6ae99b37301343778794ae5cc149de24
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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