Ethyl 4-bromobutyrate → HCID 59403493, compound

HRID 1514240Notes

Reaction equation

HRID 1514240 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]4[O:26][CH2:25][CH2:24][NH:23][CH2:22][C:21]=4[CH:27]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].CCN(C(C)C)C(C)C.Br[CH2:38][CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42]>C(#N)C.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]4[O:26][CH2:25][CH2:24][N:23]([CH2:38][CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:22][C:21]=4[CH:27]=3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 76300Ethyl 4-bromobutyrate2×HCID 81531Diisopropylethylamine2×HCID 44129142HCID 44129142, compound

Product 1

HCID 59403493HCID 59403493, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

7-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine (0.105 g, 0.272 mmol) was stirred in acetonitrile (2 ml). DIPEA (0.095 ml, 0.544 mmol) and ethyl 4-bromobutanoate (0.058 ml, 0.408 mmol) were added and the reaction mixture heated at 80° C. under Argon for 5 hours. Additional DIPEA (0.095 ml, 0.544 mmol) and ethyl 4-bromobutanoate (0.058 ml, 0.408 mmol) were added and the reaction mixture heated at 80° C. overnight. Then the reaction mixture was dissolved in EtOAc (20 ml), washed with NaHCO3 (aq) (15 ml×3) and with water (15 ml×3) and the organics dried (MgSO4) and evaporated. The crude was purified by flash chromatography eluting with EtOAc/iso-Hexane 20/30% (Biotage column), and evaporated to give the title compounds as an oil (80 mg). MS (ES): C26H3035ClN3O5 requires 499; found 500 [M+H]+.

Workup

  1. temperaturethe reaction mixture heated at 80° C. overnight
  2. washwashed with NaHCO3 (aq) (15 ml×3) and with water (15 ml×3)
  3. dry with materialthe organics dried (MgSO4)
  4. customevaporated
  5. customThe crude was purified by flash chromatography
  6. washeluting with EtOAc/iso-Hexane 20/30% (Biotage column)
  7. customevaporated

Sources & evidence

ORD record
ord-d3f62dbfc12f4123b036eb095367be04
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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