4-Methoxybenzenecarbothioamide → 2-(4-Methoxy-phenyl)-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid benzyl ester

HRID 2400370Notes

Reaction equation

HRID 2400370 reaction equation
Br[CH:2]1[C:7](=O)[CH2:6][CH2:5][N:4]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3]1.[CH3:19][O:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH2:27])=[S:26])=[CH:23][CH:22]=1>C(O)C>[CH2:12]([O:11][C:9]([N:4]1[CH2:5][CH2:6][C:7]2[N:27]=[C:25]([C:24]3[CH:28]=[CH:29][C:21]([O:20][CH3:19])=[CH:22][CH:23]=3)[S:26][C:2]=2[CH2:3]1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7368274-MethoxybenzenecarbothioamideHCID 224070023-Bromo-4-oxo-piperidine-1-carboxylic acid benzyl ester2×

Product 1

HCID 666534232-(4-Methoxy-phenyl)-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid benzyl esterYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 502 (2.0 g, 6.5 mmol) was dissolved in ethanol (20 ml). To the solution was added 4-methoxythiobenzamide (503, 1.09 g, 6.5 mmol, 1 eq) and the yellow mixture was refluxed for 17 hrs after which time TLC analysis showed full conversion of 502. The reaction mixture was concentrated in vacuo and the residue was dissolved in EtOAc, washed with 5% Na2SO4 and the organic layer was dried (MgSO4) and subsequently concentrated under reduced pressure. The resulting oil was purified by silica gel chromatography (diethyl ether, Rf 0.3) giving compound 504 in a yield of 49% as a colorless oil. Compounds having a Rb substitute can be prepared by choosing a properly substituted (Rb)-4-methoxythiobenzamide (503).

Workup

  1. temperaturethe yellow mixture was refluxed for 17 hrs after which time TLC analysis
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in EtOAc
  4. washwashed with 5% Na2SO4
  5. dry with materialthe organic layer was dried (MgSO4)
  6. concentrationsubsequently concentrated under reduced pressure
  7. customThe resulting oil was purified by silica gel chromatography (diethyl ether, Rf 0.3)

Sources & evidence

ORD record
ord-e2a5788bc90a485f9e905d75bd346c1d
Source dataset
uspto-grants-2014_08
Patent number
US08796262B2

Reaction notes

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