Ethyl bromoacetate → HCID 56598352, compound

HRID 535452Notes

Reaction equation

HRID 535452 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C(N(CC)CC)C.[OH:15][N:16]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:27]([C:29]3[N:37]4[C:32]([CH:33]=[CH:34][CH:35]=[CH:36]4)=[C:31]([O:38][CH3:39])[C:30]=3[CH3:40])=[O:28])[CH:23]=2)[NH:18][C:17]1=[O:41]>C(O)C>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][O:15][N:16]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:27]([C:29]3[N:37]4[C:32]([CH:33]=[CH:34][CH:35]=[CH:36]4)=[C:31]([O:38][CH3:39])[C:30]=3[CH3:40])=[O:28])[CH:23]=2)[NH:18][C:17]1=[O:41])[CH3:7]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetate2×HCID 8471Triethylamine2×HCID 66653429HCID 66653429, compound

Product 1

HCID 56598352HCID 56598352, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.11 ml (0.99 mmol) of ethyl bromoacetate and then 0.14 ml (0.99 mmol) of triethylamine are added, at ambient temperature under an inert atmosphere, to 0.36 g (0.99 mmol) of 3-hydroxy-6-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]quinazoline-2,4(1H,3H)-dione in 12.5 ml of ethanol. The reaction medium is stirred for 18 hours and then 0.14 ml (0.99 mmol) of triethylamine and 0.11 ml (0.99 mmol) of ethyl bromoacetate are added. After stirring for 18 hours at ambient temperature, the reaction medium is concentrated under reduced pressure. The residue obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol mixture. 217 mg of a yellow powder are obtained.

Workup

  1. stirringAfter stirring for 18 hours at ambient temperature
  2. concentrationthe reaction medium is concentrated under reduced pressure
  3. customThe residue obtained
  4. customis purified by silica gel column chromatography, elution

Sources & evidence

ORD record
ord-83fbb5dc57cb4ca481acbf8cb33185a1
Source dataset
uspto-grants-2014_10
Patent number
US08859544B2

Reaction notes

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