Benzylamine → HCID 21983564, compound

HRID 8683Notes

Reaction equation

HRID 8683 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+].[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH2:25]([NH:32][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[C:15]3[S:16][CH:17]=[CH:18][C:14]=3[O:13][N:12]=2)[CH:6]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 219835823-[3-(2-Bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole

Product 1

HCID 21983564HCID 21983564, compoundYield 81%

Procedure

The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, and benzylamine in two separate reactions using acetonitrile and 90% aqueous acetonitrile, respectively, essentially as described above in example 18 except that the reaction mixtures are filtered through 2 g of silica (ethyl acetate then dichloromethane). Combine and concentrate the appropriate fractions. Purify by column chromatography on silica gel. Elute the column with a step gradient of 50% ethyl acetate in heptane to 100% ethyl acetate to give the title compound (0.350 g, 81%). mp=60–63° C. Microanalysis (C, H, N) is consistent with the final compound.

Workup

  1. customseparate reactions
  2. customrespectively, essentially as described above in example 18 except that the reaction mixtures
  3. filtrationare filtered through 2 g of silica (ethyl acetate
  4. concentrationCombine and concentrate the appropriate fractions
  5. customPurify by column chromatography on silica gel
  6. washElute the column with a step gradient of 50% ethyl acetate in heptane to 100% ethyl acetate

Sources & evidence

ORD record
ord-c6fb58ddbaab45e5bfb690a1b57001be
Source dataset
uspto-grants-2006_08
Patent number
US07091199B1

Reaction notes

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