HCID 22507731, compound → HCID 22507713, compound

HRID 985793Notes

Reaction equation

HRID 985793 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[C:9]([CH:30]=[CH:31][N:32]=2)[C:10]([NH:12][C:13]2[S:14][C:15]3[C:21]([CH:22]4[CH2:27][O:26][CH2:25][CH2:24][O:23]4)=[CH:20][CH:19]=[C:18]([O:28][CH3:29])[C:16]=3[N:17]=2)=[O:11])[CH2:3][CH2:2]1>CO.ClCCl.[Pd]>[O:23]1[CH2:24][CH2:25][O:26][CH2:27][CH:22]1[C:21]1[C:15]2[S:14][C:13]([NH:12][C:10](=[O:11])[C:9]3[CH:30]=[CH:31][N:32]=[C:7]([CH:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)[CH:8]=3)=[N:17][C:16]=2[C:18]([O:28][CH3:29])=[CH:19][CH:20]=1

Participants

5

Reactant 1

HCID 22507731HCID 22507731, compound

Product 1

HCID 22507713HCID 22507713, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 130 mg (0.29 mmol) (±)-2-(3,6-dihydro-2H-pyran-4-yl)-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-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. Flash chromatography (2/49/49 methanol/dichloromethane/ethyl acetate) followed by trituration in ether afforded 60 mg (46%) (±)-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-(tetrahydro-pyran-4-yl)-isonicotinamide as a white crystalline solid. ES-MS m/e (%): 456 (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-dfa4ecbfa98a447bae80077de9dd4c92
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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