Ethyl 4-bromobutyrate → HCID 57505875, compound

HRID 1514213Notes

Reaction equation

HRID 1514213 reaction equation
Cl.[CH3:2][CH:3]([O:5][C:6]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:29]=[CH:28][C:22]4[CH2:23][CH2:24][NH:25][CH2:26][CH2:27][C:21]=4[CH:20]=3)[N:15]=2)=[CH:10][C:7]=1[C:8]#[N:9])[CH3:4].CCN(C(C)C)C(C)C.Br[CH2:40][CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44]>CN(C=O)C>[C:8]([C:7]1[CH:10]=[C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:29]=[CH:28][C:22]4[CH2:23][CH2:24][N:25]([CH2:40][CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:26][CH2:27][C:21]=4[CH:20]=3)[N:15]=2)[CH:12]=[CH:13][C:6]=1[O:5][CH:3]([CH3:2])[CH3:4])#[N:9]

Participants

5

Reactant 3

HCID 76300Ethyl 4-bromobutyrate2×HCID 81531DiisopropylethylamineHCID 57505874HCID 57505874, compound

Product 1

HCID 57505875HCID 57505875, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

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]+.

Workup

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

Sources & evidence

ORD record
ord-b48822b907134bd89330a6c1699e49ec
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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