Ethyl 4-bromobutyrate → HCID 59403532, compound

HRID 1514215Notes

Reaction equation

HRID 1514215 reaction equation
Cl.[F:2][C:3]([F:33])([F:32])[C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:25]=[CH:24][C:18]4[CH2:19][CH2:20][NH:21][CH2:22][CH2:23][C:17]=4[CH:16]=3)[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CCN(C(C)C)C(C)C.Br[CH2:44][CH2:45][CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48]>CN(C=O)C>[F:33][C:3]([F:2])([F:32])[C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:25]=[CH:24][C:18]4[CH2:19][CH2:20][N:21]([CH2:44][CH2:45][CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:22][CH2:23][C:17]=4[CH:16]=3)[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 76300Ethyl 4-bromobutyrate2×HCID 81531DiisopropylethylamineHCID 68469721HCID 68469721, compound

Product 1

HCID 59403532HCID 59403532, compoundYield 107.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

7-{5-[2-(Trifluoromethyl)-4-biphenylyl]-1,2,4-oxadiazol-3-yl}-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride (Example 20) (200 mg, 0.424 mmol), DIPEA (0.281 ml, 1.608 mmol) and ethyl 4-bromobutanoate (0.131 ml, 0.919 mmol) were stirred at RT in DMF (10 ml) for 5 hours. The reaction mixture was then heated to 60° C. for 5 hrs, and then allowed to stand overnight at room temperature. Further ethyl 4-bromobutanoate (0.066 ml, 0.459 mmol) was added and the reaction mixture heated at 60° C. for 6 hours. The reaction mixture was partitioned between EtOAc (˜30 ml) and water (˜30 ml) and the aqueous layer extracted once more with EtOAc (˜40 ml). The combined organics were concentrated in vacuo to yield the title compound (277 mg, 0.454 mmol) as an orange solid. MS (ES): C31H30F3N3O3 requires 549; found 550 [M+H]+.

Workup

  1. temperaturethe reaction mixture heated at 60° C. for 6 hours
  2. customThe reaction mixture was partitioned between EtOAc (˜30 ml) and water (˜30 ml)
  3. extractionthe aqueous layer extracted once more with EtOAc (˜40 ml)
  4. concentrationThe combined organics were concentrated in vacuo

Sources & evidence

ORD record
ord-8a598e5845234c1997c8466c029d84e8
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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