Water → HCID 19866472, compound

HRID 1199406Notes

Reaction equation

HRID 1199406 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][C:10]2[S:19][C:18]3[N:17]4[C:20]([CH3:23])=[N:21][N:22]=[C:16]4[CH2:15][N:14]=[C:13]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[Cl:30])[C:12]=3[CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[N:1]1([CH2:7][CH2:8][CH2:9][C:10]2[S:19][C:18]3[N:17]4[C:20]([CH3:23])=[N:21][N:22]=[C:16]4[CH2:15][NH:14][CH:13]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[Cl:30])[C:12]=3[CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19866454HCID 19866454, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19866472HCID 19866472, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.2 g (0.0027 mol) of 2-[3-(N-Morpholinyl)-n-propyl]- 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]-triazolo[4,3-a][1,4]diazepine in 20 ml of anhydrous THF are added dropwise to a prepared suspension of 0.1 g (0.0027 mol) of lithium aluminium hydride in 20 ml of anhydrous THF at ambient temperature and the mixture is refluxed for one hour. 0.1 ml of water, 0.1 ml of 15% sodium hydroxide solution and 0.3 ml of water are added to the reaction mixture which is then stirred for 30 minutes and the precipitate obtained is suction filtered. The filtrate is concentrated by evaporation, taken up in methylene chloride, washed and dried and the solvent is removed. The residue is chromatographed on silica gel using methylene chloride/methanol 95:5 as eluant. 0.16 g (yield 13%) of the desired compound are obtained, m.p. 135°-138° C.

Workup

  1. temperaturethe mixture is refluxed for one hour
  2. customthe precipitate obtained
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated by evaporation
  5. washwashed
  6. customdried
  7. customthe solvent is removed
  8. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-731dd8bce99e4f1593fe2d44c6c49433
Source dataset
uspto-grants-1990_02
Patent number
US04900729

Reaction notes

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