Water → HCID 22452742, compound

HRID 1003220Notes

Reaction equation

HRID 1003220 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([N:15]1[CH2:20][CH2:19][C:18]2[C:21]3[C:22]([S:48][C:17]=2[CH2:16]1)=[N:23][C:24]([CH2:42][N:43]1[CH:47]=[N:46][CH:45]=[N:44]1)=[C:25]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:26]=3[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=1)(=O)C1C=CC=CC=1.O>O1CCCC1>[CH3:36][O:35][C:29]1[CH:28]=[C:27]([C:26]2[C:25]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[C:24]([CH2:42][N:43]3[CH:47]=[N:46][CH:45]=[N:44]3)[N:23]=[C:22]3[S:48][C:17]4[CH2:16][NH:15][CH2:20][CH2:19][C:18]=4[C:21]=23)[CH:32]=[CH:31][C:30]=1[O:33][CH3:34]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22452759HCID 22452759, compound

Product 1

HCID 22452742HCID 22452742, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (0.164 g) was added to a solution of the compound (5.0 g) obtained in Example 20A in tetrahydrofuran (50 ml), the mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with chloroform-methanol (50:1, v/v) to yield ethyl 4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydro-2-(1,2,4-triazol-1-ylmethyl)thieno[2,3-b:5,4-c']dipyridine-3-carboxylate (3.08 g, 75%), which was then recrystallized from ethyl acetate-hexane to yield colorless prismatic crystals having a melting point of 164 to 165° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. washeluted with chloroform-methanol (50:1

Sources & evidence

ORD record
ord-34b08265febd4f579a768de8aaae4b99
Source dataset
uspto-grants-2000_04
Patent number
US06046189

Reaction notes

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