Hydrochloric Acid → Ethyl 5-(anilinocarbonothioyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylate

HRID 2093063Notes

Reaction equation

HRID 2093063 reaction equation
Cl.[CH2:2]([O:4][C:5]([C:7]1[S:8][C:9]2[CH2:10][NH:11][CH2:12][CH2:13][C:14]=2[N:15]=1)=[O:6])[CH3:3].C(N(CC)CC)C.[C:23]1([N:29]=[C:30]=[S:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl.O>[NH:29]([C:30]([N:11]1[CH2:12][CH2:13][C:14]2[N:15]=[C:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])[S:8][C:9]=2[CH2:10]1)=[S:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7673Phenyl IsothiocyanateHCID 8471TriethylamineHCID 53393419Ethyl 4,5,6,7-tetrahydrothiazolo[5,4-C]pyridine-2-carboxylate

Product 1

HCID 86650190Ethyl 5-(anilinocarbonothioyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

5-tert-butyl 2-ethyl 6,7-dihydro[1,3]thiazolo[5,4-c]pyridine-2,5(4H)-dicarboxylate obtained in step V of example 1 was deprotected to get the hydrochloride salt of 4,5,6,7-Tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid ethyl ester. To a solution of a HCl salt of 4,5,6,7-Tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid ethyl ester (1 eq) in dichloromethane, triethyl amine (1.2 eq) was added at 0° C. and the reaction mixture was stirred for 15 min. To this, a solution of phenyl isothiocyanate (1 eq) in dichloromethane was added and the reaction was continued at room temperature for 3 h. Water was added and the organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded—ethyl 5-(anilinocarbonothioyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylate.

Workup

  1. waitthe reaction was continued at room temperature for 3 h
  2. customthe organic layer was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford crude product, which
  6. customon purification by column chromatography

Sources & evidence

ORD record
ord-afa3dd686e7c41ad84adee35b07e3fb6
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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