Hydrochloric Acid → HCID 10505011, compound

HRID 1003211Notes

Reaction equation

HRID 1003211 reaction equation
C([N:9]1[CH2:14][CH2:13][C:12]2[C:15]3[C:16]([S:42][C:11]=2[CH2:10]1)=[N:17][C:18]([CH2:36][N:37]([CH2:40][CH3:41])[CH2:38][CH3:39])=[C:19]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:20]=3[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)(=O)C1C=CC=CC=1.Cl.[OH-].[Na+]>>[CH2:40]([N:37]([CH2:36][C:18]1[N:17]=[C:16]2[S:42][C:11]3[CH2:10][NH:9][CH2:14][CH2:13][C:12]=3[C:15]2=[C:20]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=2)[C:19]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:38][CH3:39])[CH3:41]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10698592HCID 10698592, compound

Product 1

HCID 10505011HCID 10505011, compoundYield 70%

Conditions

Temperature
80 °C

Procedure

A mixture of the compound obtained in Example 1A (4.02 g) and 3N HCl (12 ml) was stirred at 80° C. for 13.5 hours. After the reaction mixture was alkalinized with 1N NaOH, it was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with chloroform-methanol (30:1, v/v) to yield ethyl 2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydrothieno-[2,3-b:5,4-c']dipyridine-3-carboxylate (for structural formula, see below) (2.30 g, 70%) as an amorphous solid having a melting point of 72 to 75° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationafter which the solvent was distilled off
  5. washeluted with chloroform-methanol (30:1

Sources & evidence

ORD record
ord-cb69fcb8d63f4355a872fb495d44680b
Source dataset
uspto-grants-2000_04
Patent number
US06046189

Reaction notes

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