Water → HCID 76577927, compound

HRID 240319Notes

Reaction equation

HRID 240319 reaction equation
[C:1]([C:3]1[N:4]=[C:5]2[C:18](=[N:19][OH:20])[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:6]2=[N:7][C:8]=1[C:9]([NH2:11])=[O:10])#[N:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].O>CN(C=O)C>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][O:20][N:19]=[C:18]1[C:5]2[C:6](=[N:7][C:8]([C:9](=[O:10])[NH2:11])=[C:3]([C:1]#[N:2])[N:4]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]1=2)[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 178510554HCID 178510554, compound

Product 1

HCID 76577927HCID 76577927, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 33 (300 mg, 1.1 mmol) and Cs2CO3 (405 mg, 1.2 mmol) in DMF (15 ml), ethyl bromoacetate (0.14 ml, 1.26 mmol) was added dropwise and the mixture was stirred at 70° C. for 24 h. The suspension was cooled at room temperature, H2O (30 ml) was added and the mixture was extracted with CH2Cl2 (70 ml). The organic phase was dried over Na2SO4 and the volatile solvent was evaporated under reduced pressure. A 1:1 mixture of n-hexane/iPr2O was added and after 2 h the obtained solid was collected by filtration. The crude was purified by flash chromatography (CH2Cl2/MeOH 85:15) affording 37 (85 mg, 22%) as green-brown solid. 1H NMR (300 MHz, DMSO d6): δ 8.78 (bs, 1H), 8.73 (bs, 1H), 8.00 (dd, 1H), 7.82 (m, 2H), 7.67 (ddd, 1H), 4.87 (s, 2H), 4.19 (q, 2H), 1.25 (t, 3H). ESI+MS: calcd for C17H13N5O4: 351.32; found: 352.1 (MH+).

Workup

  1. additionwas added dropwise
  2. temperatureThe suspension was cooled at room temperature
  3. extractionthe mixture was extracted with CH2Cl2 (70 ml)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customthe volatile solvent was evaporated under reduced pressure
  6. additionA 1:1 mixture of n-hexane/iPr2O
  7. additionwas added and after 2 h the obtained solid
  8. filtrationwas collected by filtration
  9. customThe crude was purified by flash chromatography (CH2Cl2/MeOH 85:15)

Sources & evidence

ORD record
ord-1d67041e9bd3435b97d7f727522334a8
Source dataset
uspto-grants-2014_02
Patent number
US08648076B2

Reaction notes

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