Water → HCID 69433024, compound

HRID 1269722Notes

Reaction equation

HRID 1269722 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]([CH3:29])[CH2:15][CH2:16][C:17]([NH:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][N:24]=[CH:23]2)=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>O1CCCC1>[CH2:7]([N:14]([CH3:29])[CH2:15][CH2:16][CH2:17][NH:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][N:24]=[CH:23]2)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 69434289HCID 69434289, compound

Product 1

HCID 69433024HCID 69433024, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (107 mg, 2.60 mmol) was added to a solution of N3-benzyl-N1-(1H-indazol-5-yl)-N3-methyl-β-alaninamide (200 mg, 0.973 mmol) in tetrahydrofuran (30 ml) at 0° C., and the resulting mixture was refluxed for one and a half hours. Then, the reaction solution was cooled to 0° C. and a mixture of tetrahydrofuran (10 ml) and water (10 ml) was added thereto, followed by filtration. The filtrate was concentrated and the resulting residue was diluted with chloroform and washed with a 1N-aqueous sodium hydroxide solution and then a saturated aqueous sodium chloride solution. The organic layer was dried over potassium carbonate and distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=20/1) to obtain N1-benzyl-N3-(1H-indazol-5-yl)-N1-methyl-1,3-propanediamine (138 mg, 72%).

Workup

  1. temperaturethe resulting mixture was refluxed for one and a half hours
  2. additionwas added
  3. filtrationfollowed by filtration
  4. concentrationThe filtrate was concentrated
  5. additionthe resulting residue was diluted with chloroform
  6. washwashed with a 1N-aqueous sodium hydroxide solution
  7. dry with materialThe organic layer was dried over potassium carbonate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent
  10. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-88938ea8d5144c4ea2232edfb7341f9f
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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