Ethylenediamine → HCID 71279840, compound

HRID 246437Notes

Reaction equation

HRID 246437 reaction equation
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][C:23]([CH3:26])=[CH:22]4)[N:15]=2)[N:10](COCC[Si](C)(C)C)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N)CN.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C=O)C.CCOCC>[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][C:23]([CH3:26])=[CH:22]4)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 2724141Tetrabutylammonium FluorideHCID 71279970HCID 71279970, compound

Product 1

HCID 71279840HCID 71279840, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of N-tert-butyl-2-(2-methyl-1H-indol-7-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (60 mg, 126 μmol) in DMF (4 mL) was added ethylenediamine (355 mg, 399 μL, 5.9 mmol) then tetrabutylammonium fluoride (389 μL, 389 μmol). The solution was heated to 60° C. with stirring under a nitrogen atmosphere for 20 h. The reaction mixture was cooled, diluted with ether, washed water and brine, then dried (MgSO4), filtered, and concentrated in vacuo to give an oil which slowly crystallized. The crystals were triturated with water twice then dried under vacuum to give N-tert-butyl-2-(2-Methyl-1H-indol-7-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (29 mg) as a yellow solid. MS (M+H)+=348.1; 1H NMR (CDCl3) δ: 8.87 (s, 1H), 8.35 (d, J=3.0 Hz, 1H), 7.65 (d, J=7.8 Hz, 1H), 7.55-7.61 (m, 1H), 7.20-7.30 (m, 2H), 6.33-6.36 (m, 1H), 2.54 (s, 3H), 1.53 (s, 9H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an oil which
  7. customslowly crystallized
  8. customThe crystals were triturated with water twice
  9. customdried under vacuum

Sources & evidence

ORD record
ord-9eee3f7230eb4f6b862d937e295293ea
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…