N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-2-vinyl-isonicotinamide → 2-ethyl-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-isonicotinamide

HRID 1582157Notes

Reaction equation

HRID 1582157 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:13](=[O:22])[C:14]3[CH:19]=[CH:18][N:17]=[C:16]([CH:20]=[CH2:21])[CH:15]=3)[S:11][C:7]=2[C:6]([CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:5][CH:4]=1>CO.ClCCl.[Pd]>[CH2:20]([C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][N:17]=1)[C:13]([NH:12][C:10]1[S:11][C:7]2[C:6]([CH:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=2[N:9]=1)=[O:22])[CH3:21]

Participants

5

Reactant 1

HCID 22719569N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-2-vinyl-isonicotinamide

Product 1

HCID 101266742-ethyl-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-isonicotinamideYield 88%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 90 mg (0.23 mmol) N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-2-vinyl-isonicotinamide in 10 ml methanol and 10 ml dichloromethane was added a spatula end of 10% palladium on charcoal and the mixture was then stirred for 16 h at room temperature under an atmosphere of hydrogen. The mixture was then filtered, washing with dichloromethane, and the filtrate concentrated in vacuo and triturated in ether to afford 80 mg (88%) 2-ethyl-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-isonicotinamide as a yellow solid. ES-MS m/e (%): 398 (M+H+, 100).

Workup

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

Sources & evidence

ORD record
ord-7b7e82a5967a4c62a4db324688ba4cc1
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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