Water → HCID 86760410, compound

HRID 349576Notes

Reaction equation

HRID 349576 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([N:26]1[C:33]2[N:29]([N:30]=[CH:31][C:32]=2[CH2:34][CH2:35][C:36]([NH2:38])=O)[CH2:28][CH2:27]1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[F-].[Na+].[OH2:41].O1CCC[CH2:43]1>>[C:7]([N:26]1[C:33]2[N:29]([N:30]=[CH:31][C:32]=2[CH2:34][CH2:35][CH2:36][NH:38][CH:43]=[O:41])[CH2:28][CH2:27]1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 5

HCID 962WaterHCID 5235Sodium FluorideHCID 8028TetrahydrofuranHCID 17961983HCID 17961983, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 86760410HCID 86760410, compound

Procedure

To a suspension of lithium aluminum hydride (1.8 g) in tetrahydrofuran (200 ml) was added 3-(1-trityl-2,3-dihydro-1H-imidazo[1,2-b]pyrazol-7-yl)propanamide (10 g) at room temperature. The mixture was stirred at room temperature for 2.5 hours. After cooling on an ice bath, sodium fluoride (7.95 g) and water (3.4 ml) were added to the reaction mixture. The insoluble materials were removed by filtration. To the filtrate was added ethyl formate, and the mixture was refluxed for 24 hours. After evaporation of the solvent in vacuo, the residue was triturated with diisopropyl ether and dried in vacuo to give 3-(1-trityl-2,3-dihydro-1H-imidazo[1,2-b]pyrazol-7-yl)propylformamide (6.62 g).

Workup

  1. temperatureAfter cooling on an ice bath
  2. customThe insoluble materials were removed by filtration
  3. additionTo the filtrate was added ethyl formate
  4. temperaturethe mixture was refluxed for 24 hours
  5. customAfter evaporation of the solvent in vacuo
  6. customthe residue was triturated with diisopropyl ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-3f6b1012e2b148edbd3daa80410da394
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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