Ethyl bromoacetate → HCID 59146172, compound

HRID 1512792Notes

Reaction equation

HRID 1512792 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].CCN(CC)CC.[Cl:15][C:16]1[CH:17]=[C:18]([C:26]2[O:30][N:29]=[C:28]([C:31]3[CH:32]=[CH:33][CH:34]=[C:35]4[C:39]=3[NH:38][CH:37]=[C:36]4[CH2:40][CH2:41][NH2:42])[N:27]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH:23]([CH3:25])[CH3:24]>C1(C)C=CC=CC=1>[Cl:15][C:16]1[CH:17]=[C:18]([C:26]2[O:30][N:29]=[C:28]([C:31]3[CH:32]=[CH:33][CH:34]=[C:35]4[C:39]=3[NH:38][CH:37]=[C:36]4[CH2:40][CH2:41][NH:42][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[N:27]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH:23]([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 59146144HCID 59146144, compound

Product 1

HCID 59146172HCID 59146172, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl bromoacetate (167 mg) and Et3N (101 mg) were added to the solution of 2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]ethanamine (D84) (530 mg) in toluene (3 mL). The resulting reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated and the residue was purified by Mass Directed Auto Prep to afford ethyl N-{2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]ethyl}glycinate (D86) (132 mg) as a yellow solid. MS (ES): C25H27ClN4O4 requires 482; found 483.2 (M+H+).

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by Mass Directed Auto Prep

Sources & evidence

ORD record
ord-375f18bf5ee7400bbf296efc03866e8a
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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