Triethylamine → 4-(3,4-Dihydro-1H-benzo[4,5]thieno[2,3-c]pyridine-2-sulfonylmethyl)-tetrahydro-pyran-4-carboxylic acid

HRID 1582044Notes

Reaction equation

HRID 1582044 reaction equation
C[O:2][C:3]([C:5]1([CH2:11][S:12](Cl)(=[O:14])=[O:13])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].Cl.[CH2:17]1[C:22]2[S:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:21]=2[CH2:20][CH2:19][NH:18]1.C(N(CC)CC)C.O.[OH-].[Li+]>O1CCCC1.CO.O>[CH2:17]1[C:22]2[S:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:21]=2[CH2:20][CH2:19][N:18]1[S:12]([CH2:11][C:5]1([C:3]([OH:2])=[O:4])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)(=[O:14])=[O:13]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 168937Lithium hydroxide, monohydrateHCID 122652651,2,3,4-Tetrahydro-[1]benzothieno[2,3-c]pyridine hydrochlorideHCID 22228396Methyl 4-[(chlorosulfonyl)methyl]oxane-4-carboxylate

Product 1

HCID 102007324-(3,4-Dihydro-1H-benzo[4,5]thieno[2,3-c]pyridine-2-sulfonylmethyl)-tetrahydro-pyran-4-carboxylic acidYield 25.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Chlorosulfonylmethyl-tetrahydro-pyran-4-carboxylic acid methyl ester (520 mg) was added to a solution of 1,2,3,4-tetrahydrobenzo[4,5]thieno[2,3-c]pyridine hydrochloride (450 mg) and triethlyamine (1.0 ml) in tetrahydrofuran (20 ml). The mixture was stirred at room temperature for 18 h then water (5 ml), methanol (5 ml) and lithium hydroxide monohydrate (400 mg) were added and the reaction heated to reflux for 3 h. The mixture was evaporated under reduced pressure and the aqueous residue washed with diethyl ether (2×10 ml), acidified with 1M hydrochloric acid and the precipitate collected by filtration to give the title compound (200 mg, 25%) as a white solid.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 3 h
  3. customThe mixture was evaporated under reduced pressure
  4. washthe aqueous residue washed with diethyl ether (2×10 ml)
  5. filtrationthe precipitate collected by filtration

Sources & evidence

ORD record
ord-5a34ba2fd0e4411da5ce9f532c089442
Source dataset
uspto-grants-2004_05
Patent number
US06734189B2

Reaction notes

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