Tetrahydrofuran → HCID 15462643, compound

HRID 1003218Notes

Reaction equation

HRID 1003218 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[N:12]=[C:11]2[S:13][C:14]3[CH2:15][NH:16][CH2:17][CH2:18][C:19]=3[C:10]2=[C:9]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[C:8]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:4][CH3:5])[CH3:2].[C:35](Cl)(=[O:39])[O:36][CH2:37][CH3:38].C(=O)([O-])[O-].[K+].[K+].O1CCCC1>O>[CH2:4]([N:3]([CH2:6][C:7]1[N:12]=[C:11]2[S:13][C:14]3[CH2:15][N:16]([C:35]([O:36][CH2:37][CH3:38])=[O:39])[CH2:17][CH2:18][C:19]=3[C:10]2=[C:9]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[C:8]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:1][CH3:2])[CH3:5]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 10505011HCID 10505011, compound

Product 1

HCID 15462643HCID 15462643, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the compound obtained in Example 5A (1.12 g), ethyl chlorocarbonate (0.35 g), potassium carbonate (0.47 g) and tetrahydrofuran (20 ml) was stirred at room temperature for 3 hours. The reaction mixture was poured over water and 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 ethyl acetate-hexane (1:1, v/v) to yield ethyl 2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-7-ethoxycarbonyl-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine-3-carboxylate (for structural formula, see below) (0.89 g, 56%), which was then recrystallized from ethyl acetate-hexane to yield colorless prismatic crystals having a melting point of 119 to 120° C. ##STR54##

Workup

  1. extractionextracted 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 ethyl acetate-hexane (1:1

Sources & evidence

ORD record
ord-301ee55fa8524f96b15b09538744aa53
Source dataset
uspto-grants-2000_04
Patent number
US06046189

Reaction notes

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