Potassium Carbonate → Pyridin-3-ylmethyl-[2-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-ethyl]-amine

HRID 8665

Reaction equation

HRID 8665 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:11]2[C:15]3[S:16][CH:17]=[CH:18][C:14]=3[O:13][N:12]=2)[CH:8]=[CH:9][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1>C(#N)C>[N:29]1[CH:30]=[CH:31][CH:32]=[C:27]([CH2:26][NH:25][CH2:2][CH2:3][O:4][C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([C:11]3[C:15]4[S:16][CH:17]=[CH:18][C:14]=4[O:13][N:12]=3)[CH:6]=2)[CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 310183-PyridinemethanamineHCID 219835823-[3-(2-Bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole

Product 1

HCID 21983571Pyridin-3-ylmethyl-[2-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-ethyl]-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 3-(aminomethyl)pyridine and acetonitrile essentially as described above in example 18 except that the Waters Sep-Pak filtration is eluted with 10% methanol in dichloromethane and the column is eluted using a graded solvent mixture of 2% methanol in dichloromethane, to 6% methanol in dichloromethane. Purity by LC/MS (APCI)=100%, [M+H]+=352.

Workup

  1. filtrationas described above in example 18 except that the Waters Sep-Pak filtration
  2. washis eluted with 10% methanol in dichloromethane
  3. washthe column is eluted
  4. additiona graded solvent mixture of 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-7f2d65abc2e648ce8229b3de35ed1ffc
Source dataset
uspto-grants-2006_08
Patent number
US07091199B1

Linked notes

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