Ethylenediamine → HCID 75203176, compound

HRID 1519136Notes

Reaction equation

HRID 1519136 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[NH:13][N:12](COCC[Si](C)(C)C)[NH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.C(N)CN.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CCOC(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:10]=[N:11][NH:12][N:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 2724141Tetrabutylammonium FluorideHCID 86724057HCID 86724057, compound

Product 1

HCID 75203176HCID 75203176, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To N-(3-fluorophenyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,3-triazol-5-amine 7e (50 mg, 0.16 mmol) was added ethane-1,2-diamine (50 mg, 55.6 μL, 0.83 mmol) and tetrabutylammonium fluoride (424 mg, 478 μL, 1.62 mmol) and the mixture was heated to 90° C. in a microwave for 2 h. The mixture was diluted with EtOAc and water and the organic was washed with water, brine and then dried (MgSO4) and concentrated. Material was purified by Fractionlynx to afford the title compound I-45 as a white solid (10 mg, 35%). 1H NMR (500 MHz, d6-DMSO) δ 14.19 (1H, s), 9.02 (1H, s), 7.39 (1H, d), 7.17-7.27 (2H, m), 6.99-7.06 (1H, m), 6.52-6.61 (1H, m). MS m/z: 179.1 (M+H)+.

Workup

  1. washthe organic was washed with water, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customMaterial was purified by Fractionlynx

Sources & evidence

ORD record
ord-fddc66b911c34f0b8877f77dc459ab5e
Source dataset
uspto-grants-2015_07
Patent number
US09073875B2

Reaction notes

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