Ethyl 4-bromobutyrate → HCID 68466841, compound

HRID 1514239Notes

Reaction equation

HRID 1514239 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:20]=[CH:21][C:22]4[O:28][CH2:27][CH2:26][NH:25][CH2:24][C:23]=4[CH:29]=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]>C(#N)C.CCOC(C)=O>[C:8]([C:7]1[CH:10]=[C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[CH:21][C:22]4[O:28][CH2:27][CH2:26][N:25]([CH2:40][CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:24][C:23]=4[CH:29]=3)[N:15]=2)[CH:12]=[CH:13][C:6]=1[O:5][CH:3]([CH3:2])[CH3:4])#[N:9]

Participants

6

Reactant 3

HCID 76300Ethyl 4-bromobutyrate2×HCID 81531Diisopropylethylamine2×HCID 68469090HCID 68469090, compound

Product 1

HCID 68466841HCID 68466841, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-[(1-methylethyl)oxy]-5-[3-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1,2,4-oxadiazol-5-yl]benzonitrile hydrochloride (Example 35) (0.104 g, 0.276 mmol) was stirred in acetonitrile (2 ml). DIPEA (0.097 ml, 0.553 mmol) and ethyl 4-bromobutanoate (0.059 ml, 0.414 mmol) were added and the reaction mixture stirred and heated at 80° C. under Argon for 6 hours. Additional ethyl 4-bromobutanoate (0.059 ml, 0.414 mmol) and DIPEA (0.097 ml, 0.553 mmol) were added and the reaction mixture stirred and heated at 80° C. under argon overnight. Then the reaction mixture was dissolved in EtOAc, washed with saturated NaHCO3 solution (3×15 ml) and water (15 ml) and the organics dried (MgSO4) and evaporated. The crude was purified by flash chromatography, eluting with EtOAc/iso-Hexane 10-20% (Biotage Column) and evaporated to give the title compound (84 mg) as an oil. MS (ES): C27H30N4O5 requires 490; found 491 [M+H]+.

Workup

  1. stirringthe reaction mixture stirred
  2. temperatureheated at 80° C. under argon overnight
  3. washwashed with saturated NaHCO3 solution (3×15 ml) and water (15 ml)
  4. dry with materialthe organics dried (MgSO4)
  5. customevaporated
  6. customThe crude was purified by flash chromatography
  7. washeluting with EtOAc/iso-Hexane 10-20% (Biotage Column)
  8. customevaporated

Sources & evidence

ORD record
ord-be7ec4d8076144f19442a778d9b4cc16
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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