Ethyl bromoacetate → Ethyl [9-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]acetate

HRID 1514242Notes

Reaction equation

HRID 1514242 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:12]=[CH:11][C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[C:28]4[O:27][CH2:26][CH2:25][NH:24][CH2:23][C:22]=4[CH:21]=[CH:20][CH:19]=3)[N:14]=2)=[CH:9][C:6]=1[C:7]#[N:8])[CH3:3].C(N(CC)C(C)C)(C)C.Br[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]>C(#N)C>[C:7]([C:6]1[CH:9]=[C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[C:28]4[O:27][CH2:26][CH2:25][N:24]([CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:23][C:22]=4[CH:21]=[CH:20][CH:19]=3)[N:14]=2)[CH:11]=[CH:12][C:5]=1[O:4][CH:2]([CH3:1])[CH3:3])#[N:8]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 44129064HCID 44129064, compound

Product 1

HCID 59403531Ethyl [9-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]acetateYield 96.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-[(1-methylethyl)oxy]-5-[3-(2,3,4,5-tetrahydro-1,4-benzoxazepin-9-yl)-1,2,4-oxadiazol-5-yl]benzonitrile (Example 32) (110 mg, 0.224 mmol) in acetonitrile (10 mL) was added N,N-diisopropylethylamine (0.08 mL, 0.449 mmol) and ethyl bromoacetate (0.05 mL, 0.449 mmol). The reaction mixture was heated to 80° C. for 2 hours. The mixture was allowed to cool to room temperature. The solvent was evaporated to give the title compound as a brown solid (100 mg).

Workup

  1. temperatureto cool to room temperature
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c82ae89db7f8407087355b4da4076e07
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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