N-Iodosuccinimide → HCID 178501068, compound

HRID 1878914Notes

Reaction equation

HRID 1878914 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]2=[CH:9][N:10]=[C:11]([C@H:12]3[CH2:17][CH2:16][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:13]3)[N:4]2[N:3]=1.[I:22]N1C(=O)CCC1=O>CN(C=O)C>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]2=[C:9]([I:22])[N:10]=[C:11]([C@H:12]3[CH2:13][CH2:14][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:16][CH2:17]3)[N:4]2[N:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178501056HCID 178501056, compound

Product 1

HCID 178501068HCID 178501068, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl trans-4-(2-amino-4-oxo-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-7-yl)cyclohexanecarboxylate (0.200 g, 0.000686 mol) and N-iodosuccinimide (0.278 g, 0.00124 mol) in anhydrous DMF (4.0 mL) was stirred at rt for 48 h. The reaction was concentrated in vacuo then partitioned between H2O and EtOAc. The aqueous material was re-extracted with EtOAc (3×) and the combined organic fractions were washed with H2O (2×), Na2S2O3 (2×) and brine (1×). The aqueous was re-extracted with CHCl3 and combined with the EtOAc fractions dried over Na2SO4, filtered and concentrated in vacuo resulting in 229 mg, (79.9% yield) of the title compound as a light orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.34-1.65 (m, 4H), 1.88-2.06 (m, 4H), 2.33-2.45 (m, 1H), 2.91-3.01 (m, 1H), 3.61 (s, 3H), 6.17 (s, 2H) and 10.82 (br. s., 1H); MS (ES+): m/z 417.82 [MH+].

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthen partitioned between H2O and EtOAc
  3. extractionThe aqueous material was re-extracted with EtOAc (3×)
  4. washthe combined organic fractions were washed with H2O (2×), Na2S2O3 (2×) and brine (1×)
  5. extractionThe aqueous was re-extracted with CHCl3
  6. dry with materialfractions dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ca60398cbb1941699b9abd4d635a2180
Source dataset
uspto-grants-2012_11
Patent number
US08314111B2

Reaction notes

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