Ethyl bromoacetate → HCID 53936007, compound

HRID 1531736Notes

Reaction equation

HRID 1531736 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:11]([NH:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[N:21]([CH3:25])[C:20](=[O:26])[C:19]([CH2:27][C:28]2[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=2)=[N:18]3)(=[O:13])=[O:12])[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:39][C:40]([O:42][CH2:43]C)=[O:41]>O1CCCC1>[CH3:43][O:42][C:40]([CH2:39][N:14]([S:11]([C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[N:1]=[CH:2][CH:3]=[CH:4]2)(=[O:12])=[O:13])[C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]([CH3:25])[C:20](=[O:26])[C:19]([CH2:27][C:28]1[CH:29]=[CH:30][C:31]([C:32]#[N:33])=[CH:34][CH:35]=1)=[N:18]2)=[O:41]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 21250244HCID 21250244, compound

Product 1

HCID 53936007HCID 53936007, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 g (4.15 mmol) of 4-{[6-(quinolin-8-yl-sulphonylamino)-1-methyl-2-oxo-1,2-dihydroquinoxalin-3-yl]-methyl}-benzonitrile are dissolved in 150 ml tetrahydrofuran and after the addition of 0.2 g (4.15 mmol) of sodium hydride (50% in oil) stirred for 2 hours at ambient temperature. After the addition of 0.47 ml (4.15 mmol) of ethyl bromoacetate the reaction mixture was stirred for 5 hours. The precipitate is suction filtered, the mother liquor is evaporated down and chromatographed on silica gel, eluting initially with petroleum ether and then with petroleum ether/ethyl acetate (55:45). The desired fractions are combined and evaporated down.

Workup

  1. stirringwas stirred for 5 hours
  2. filtrationfiltered
  3. customthe mother liquor is evaporated down
  4. customchromatographed on silica gel
  5. washeluting initially with petroleum ether
  6. customevaporated down

Sources & evidence

ORD record
ord-588be961b5754a3ea71ba4e0da021a49
Source dataset
uspto-grants-2001_03
Patent number
US06200976B1

Reaction notes

Loading…