Ethyl 4-bromobutyrate → HCID 57505875, compound

Participants

Reaction Conditions

Reaction Steps

2-[(1-Methylethyl)oxy]-5-[3-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-1,2,4-oxadiazol-5-yl]benzonitrile hydrochloride (Example 18) (200 mg, 0.534 mmol), DIPEA (0.327 ml, 1.869 mmol) and ethyl 4-bromobutanoate (0.153 ml, 1.068 mmol) were stirred at room temperature in DMF (10 ml) for 5 hours, the reaction mixture then heated to 60° C. for 5 h, the reaction mixture was allowed to stand overnight at room temperature, further ethyl 4-bromobutanoate (0.076 ml, 0.534 mmol) was added and the reaction mixture heated at 60° C. for 6 hours. The reaction mixture was partitioned between ethylacetate (˜30 ml) and water (˜30 ml) and the aq. layer extracted once more with ethylacetate (˜40 ml). The combined organics were concentrated in vacuo to yield the title compound (218 mg, 0.402 mmol) as an orange oil. MS (ES): C28H32N4O4 requires 488; found 489 [M+H]+.

Provenance & Evidence