Ethyl bromoacetate → HCID 56960508, compound

HRID 1626353Notes

Reaction equation

HRID 1626353 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[CH:36]=[CH:35][C:12]([O:13][C:14]3[N:19]=[CH:18][N:17]=[C:16]([O:20][CH:21]4[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]4)[C:15]=3[CH3:34])=[CH:11][CH:10]=2)[S:3]1.[H-].[Na+].Br[CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42]>CN(C)C=O>[CH2:44]([O:43][C:41](=[O:42])[CH2:40][N:6]1[C:5](=[O:7])/[C:4](=[CH:8]/[C:9]2[CH:10]=[CH:11][C:12]([O:13][C:14]3[N:19]=[CH:18][N:17]=[C:16]([O:20][CH:21]4[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])[CH2:23][CH2:22]4)[C:15]=3[CH3:34])=[CH:35][CH:36]=2)/[S:3][C:2]1=[O:1])[CH3:45]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 76449518HCID 76449518, compound

Product 1

HCID 56960508HCID 56960508, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of tert-butyl 4-((6-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)-5-methylpyrimidin-4-yl)oxy)piperidine-1-carboxylate (250 mg, 0.0004882 mole) in dimethyl formamide (10 ml), sodium hydride (50%, 23.4 mg, 0.0004882 mole) was added at 0° C. and reaction mixture was stirred for 1 hours 30° C. and then ethyl bromoacetate (0.08 ml, 0.000733 mole) was added at 0° C., then reaction mixture was stirred for 3 hours at 30° C. Then reaction mixture was poured into ice cold water and extracted with ethyl acetate. Organic extract was washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure to yield crude product. Then crude product was purified through column chromatography using 18% ethyl acetate in hexane as an eluent to yield the product as white solid (160 mg). 1HNMR: δ 1.30 (t, J=7.0 Hz, 3H), 1.48 (s, 9H), 1.76-1.81 (m, 2H), 1.96-2.01 (m, 2H), 2.18 (s, 3H), 3.34-3.41 (m, 2H), 3.71-3.76 (m, 2H), 4.25 (q, J=7.2 Hz, 2H), 4.48 (s, 2H), 5.33-5.35 (m, 1H), 7.55 (d, J=9.6 Hz, 2H), 7.57 (d, J=8.4 Hz, 2H), 7.93 (s, 1H), 8.25 (s, 1H).

Workup

  1. customreaction mixture
  2. customreaction mixture
  3. stirringwas stirred for 3 hours at 30° C
  4. customThen reaction mixture
  5. additionwas poured into ice cold water
  6. extractionextracted with ethyl acetate
  7. extractionOrganic extract
  8. washwas washed with water and brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated under reduced pressure
  11. customto yield crude product
  12. customThen crude product was purified through column chromatography

Sources & evidence

ORD record
ord-b6238fef23bf49d5822e734e773b16e4
Source dataset
uspto-grants-2014_07
Patent number
US08785463B2

Reaction notes

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