Water → HCID 76577930, compound

HRID 240322Notes

Reaction equation

HRID 240322 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+].[CH2:27]([O:29][C:30](=[O:37])[CH2:31][NH:32][C:33](=[O:36])[CH2:34]Br)[CH3:28].O>CN(C=O)C>[CH2:27]([O:29][C:30](=[O:37])[CH2:31][NH:32][C:33](=[O:36])[CH2:34][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)[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 96555N-(Bromoacetyl)glycine, ethyl esterHCID 178510554HCID 178510554, compound

Product 1

HCID 76577930HCID 76577930, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 33 (212 mg, 0.80), Cs2CO3 (260 mg, 0.80) in DMF (15 ml), 39 (200 mg, 0.89 mmol) was added portionwise and the mixture was stirred at room temperature for 2 days. H2O (30 ml) was added and the suspension was extracted with CH2Cl2 (70 ml). The organic phase was dried over Na2SO4 and the solvent was evaporated under reduced pressure. The crude was purified by flash chromatography (CH2Cl2/MeOH 9:1) affording 40 (56 mg, 17%) as yellow-brown solid. 1H NMR (300 MHz, DMSO d6): δ 8.78 (m, 2H), 8.12 (bs, 1H), 8.05-7.78 (m, 3H), 7.67 (m, 1H), 4.72 and 4.69 (s, 2H), 4.10 (q, 2H), 3.92 and 3.90 (s, 2H), 1.19 (t, 3H). ESI+MS: calcd for C19H16N6O5: 408.38; found: 409.1 (MH+).

Workup

  1. additionwas added portionwise
  2. extractionthe suspension was extracted with CH2Cl2 (70 ml)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customthe solvent was evaporated under reduced pressure
  5. customThe crude was purified by flash chromatography (CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-7febceee04f14e77a96b4dbd71eaf4e4
Source dataset
uspto-grants-2014_02
Patent number
US08648076B2

Reaction notes

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