Ethylenediamine → HCID 58010104, compound

HRID 1854471Notes

Reaction equation

HRID 1854471 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:30](COCC[Si](C)(C)C)[C:16]2[N:17]=[CH:18][C:19]3[N:20]([C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[N:22][CH:23]=3)[C:15]=2[CH:14]=1.C(N)CN.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[NH:30][C:16]2[N:17]=[CH:18][C:19]3[N:20]([C:21]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[N:22][CH:23]=3)[C:15]=2[CH:14]=1

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 2724141Tetrabutylammonium FluorideHCID 58009855HCID 58009855, compound

Product 1

HCID 58010104HCID 58010104, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

7-(5-Methoxy-1-methyl-1H-indol-3-yl)-1-phenyl-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.054 g, 0.103 mmol) in DMF (3 mL) was treated with ethylenediamine (0.207 ml, 3.09 mmol) and TBAF (1 M in THF, 0.412 mL, 0.412 mmol). The solution was heated to about 90° C. for about 70 min. The mixture was cooled to ambient temperature and the mixture was diluted with EtOAc (10 mL), washed with water (6 mL), dried over anhydrous MgSO4, filtered, and concentrated to give a yellow residue. The residue was purified by silica gel chromatography eluting with 1-6% MeOH/DCM to provide a yellow solid. The solid was triturated with heptane (2 mL) to provide 7-(5-methoxy-1-methyl-1H-indol-3-yl)-1-phenyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.004 g, 10%): LC/MS (Table 2, Method a) Rt=2.26 min; MS m/z: 394 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. washwashed with water (6 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow residue
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 1-6% MeOH/DCM
  9. customto provide a yellow solid
  10. customThe solid was triturated with heptane (2 mL)

Sources & evidence

ORD record
ord-ee6bc3cff62e4ca694d2019865231cac
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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