Ethanol → HCID 22452740, compound

HRID 1003221Notes

Reaction equation

HRID 1003221 reaction equation
ClC1C=CC(C([N:8]2[CH2:13][CH2:12][C:11]3[C:14]4[C:15]([S:43][C:10]=3[CH2:9]2)=[N:16][C:17]([CH2:37][N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])=[C:18]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:19]=4[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH:27]([CH3:29])[CH3:28])=[C:22]([O:30][CH3:31])[CH:21]=2)=O)=CC=1.[OH-].[K+].C(O)C>O>[CH2:41]([N:38]([CH2:37][C:17]1[N:16]=[C:15]2[S:43][C:10]3[CH2:9][NH:8][CH2:13][CH2:12][C:11]=3[C:14]2=[C:19]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH:27]([CH3:29])[CH3:28])=[C:22]([O:30][CH3:31])[CH:21]=2)[C:18]=1[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:39][CH3:40])[CH3:42]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 22452760HCID 22452760, compound

Product 1

HCID 22452740HCID 22452740, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the compound (8.9 g) obtained in Example 48A, 4N KOH (18 ml) and ethanol (150 ml) was stirred under refluxing conditions for 5 hours. The reaction mixture was poured over water 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 ethyl acetate-hexane (4:1, v/v) to yield ethyl 2-diethylaminomethyl-4-(4-isopropoxy-3-methoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine-3-carboxylate (6.5 g, 88%), which was then recrystallized from ethyl acetate-hexane to yield colorless prismatic crystals.

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 ethyl acetate-hexane (4:1

Sources & evidence

ORD record
ord-c9e38c8572814d138ece233766ae4577
Source dataset
uspto-grants-2000_04
Patent number
US06046189

Reaction notes

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