Potassium Carbonate → 4-{[3-(3-Thieno[2,3-d]isoxazol-3-yl-phenoxy)-propylamino]-methyl}-benzenesulfonamide

HRID 8655

Reaction equation

HRID 8655 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[C:16]3[S:17][CH:18]=[CH:19][C:15]=3[O:14][N:13]=2)[CH:9]=[CH:10][CH:11]=1.ClCCCOC1C=C(C2C3SC=CC=3ON=2)C=CC=1.O.Cl.[NH2:41][CH2:42][C:43]1[CH:48]=[CH:47][C:46]([S:49]([NH2:52])(=[O:51])=[O:50])=[CH:45][CH:44]=1.C(=O)([O-])[O-].[K+].[K+]>>[O:14]1[C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:12]([C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=2)[O:5][CH2:4][CH2:3][CH2:2][NH:41][CH2:42][C:43]2[CH:44]=[CH:45][C:46]([S:49]([NH2:52])(=[O:50])=[O:51])=[CH:47][CH:48]=2)=[N:13]1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 215845674-(Aminomethyl)benzenesulfonamide hydrochloride hydrateHCID 219835563-[3-(3-Chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazoleHCID 219835593-[3-(3-Bromo-propoxy)phenyl]-thieno[2,3-d]isoxazole

Product 1

HCID 219835724-{[3-(3-Thieno[2,3-d]isoxazol-3-yl-phenoxy)-propylamino]-methyl}-benzenesulfonamideYield 27%

Procedure

The title compound is prepared from a mixture of 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-[3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 4-(aminomethyl) benzenesulfonamide hydrochloride monohydrate and potassium carbonate essentially as described above in example 4 except that the column is eluted using a graded solvent mixture of dichloromethane:methanol (95:5). Combine the appropriate fractions and concentrate to give the title compound (0.12 g, 27% Yield) as a solid. Purity by LC/MS (APCI)=100% area, [M+H]+=444 m/e.

Workup

  1. washis eluted
  2. additiona graded solvent mixture of dichloromethane:methanol (95:5)
  3. concentrationCombine the appropriate fractions and concentrate

Sources & evidence

ORD record
ord-c0f1ba7fd1aa4441a926a53d857380d8
Source dataset
uspto-grants-2006_08
Patent number
US07091199B1

Linked notes

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