[7-(3,6-dihydro-2H-pyran-4-yl)-4-methoxy-benzothiazol-2-yl]-carbamic acid methyl ester → [4-Methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-carbamic acid methyl ester

HRID 1582101Notes

Reaction equation

HRID 1582101 reaction equation
[CH3:1][O:2][C:3](=[O:22])[NH:4][C:5]1[S:6][C:7]2[C:13]([C:14]3[CH2:15][CH2:16][O:17][CH2:18][CH:19]=3)=[CH:12][CH:11]=[C:10]([O:20][CH3:21])[C:8]=2[N:9]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:22])[NH:4][C:5]1[S:6][C:7]2[C:13]([CH:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[CH:12][CH:11]=[C:10]([O:20][CH3:21])[C:8]=2[N:9]=1

Participants

4

Reactant 1

HCID 10171949[7-(3,6-dihydro-2H-pyran-4-yl)-4-methoxy-benzothiazol-2-yl]-carbamic acid methyl ester

Product 1

HCID 86588829[4-Methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-carbamic acid methyl esterYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 200 mg (0.62 mmol) [7-(3,6-dihydro-2H-pyran-4-yl)-4-methoxy-benzothiazol-2-yl]-carbamic acid methyl ester in 20 ml methanol was added a spatula end of 10% palladium on charcoal and the mixture was then stirred for 72 h at room temperature under an atmosphere of hydrogen. The mixture was then filtered, washing with dichloromethane, and the filtrate concentrated in vacuo to afford 130 mg (64%) [4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-carbamic acid methyl ester as an off-white foam. ES-MS m/e (%): 345 (M+Na+, 9), 323 (M+H+, 100).

Workup

  1. filtrationThe mixture was then filtered
  2. washwashing with dichloromethane
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-6c001e6082954c94a2aa463030599196
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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