Water → 4-(3-Aminopropyl)-1-(2-triphenylmethyloxyethyl)-5-aminopyrazole

HRID 349553Notes

Reaction equation

HRID 349553 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7](/[CH:9]=[CH:10]/[C:11]1[CH:12]=[N:13][N:14]([CH2:17][CH2:18][O:19][C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]=1[NH2:16])#[N:8].[F-].[Na+].O>O1CCCC1>[NH2:8][CH2:7][CH2:9][CH2:10][C:11]1[CH:12]=[N:13][N:14]([CH2:17][CH2:18][O:19][C:20]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]=1[NH2:16]

Participants

6

Reactant 4

HCID 962WaterHCID 5235Sodium FluorideHCID 179619694-[(E)-2-cyanoethenyl]-1-[2-(trityloxy)ethyl]-5-aminopyrazoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 179619934-(3-Aminopropyl)-1-(2-triphenylmethyloxyethyl)-5-aminopyrazoleYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (5.41 g) in tetrahydrofuran (200 ml) was added a solution of 4-[(E)-2-cyanoethenyl]-1-[2-(trityloxy)ethyl]-5-aminopyrazole (15 g) in tetrahydrofuran (100 ml) under ice-cooling. The mixture was refluxed for 3.5 hours. After cooling on an ice bath, sodium fluoride (24 g) and water (10.3 ml) were added to the reaction mixture. The insoluble materials were removed by filtration. The filtrate was concentrated in vacuo to give 4-(3-aminopropyl)-1-(2-triphenylmethyloxyethyl)-5-aminopyrazole (13.7 g). This product was used in the next step without further purification.

Workup

  1. temperaturecooling
  2. temperatureThe mixture was refluxed for 3.5 hours
  3. temperatureAfter cooling on an ice bath
  4. customThe insoluble materials were removed by filtration
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f466e2e378d24b20abc8830681963482
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

Loading…