Potassium Iodide → HCID 58529656, compound

HRID 1972713Notes

Reaction equation

HRID 1972713 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11](=[O:14])[CH2:12]Cl)[N:6]2[N:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[I-].[K+].[CH2:23]([N:30]1[CH2:35][CH2:34][NH:33][CH:32]([CH2:36][O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11](=[O:14])[CH2:12][N:33]3[CH2:34][CH2:35][N:30]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:31][CH:32]3[CH2:36][O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:39])[CH3:40])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 585293111-{4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl}-2-chloroethan-1-oneHCID 58529880HCID 58529880, compound

Product 1

HCID 58529656HCID 58529656, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-2-chloroethanone (1.00 g, 4.75 mmol), K2CO3 (1.97 g, 14.2 mmol) and potassium iodide (79 mg, 0.47 mmol) in DMF (20 mL), was added 1-benzyl-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)piperazine (1.53 g, 4.79 mmol, prepared by the method of Naylor et al J. Med. Chem. 36, 2075). The reaction was allowed to stir for 17 hours. The mixture was partitioned between ethyl acetate (200 mL) and saturated, aqueous Na2CO3 solution (100 mL). The layers were separated and the organic was washed with brine, dried (Na2SO4), and evaporated. The crude material was purified by ISCO® chromatography using a gradient elution from 50% to 100% ethyl acetate in hexanes to obtain 1.9 g (81%) of the desired product LC-MS [M+H]+=495.6, RT=2.56 min.

Workup

  1. customprepared by the method of Naylor et al J
  2. customThe mixture was partitioned between ethyl acetate (200 mL)
  3. customThe layers were separated
  4. washthe organic was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe crude material was purified by ISCO® chromatography
  8. washa gradient elution from 50% to 100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-3b4125b3c1ed4951ab17abb723b4d053
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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