Ethylamine → HCID 25139025, compound

HRID 1669186Notes

Reaction equation

HRID 1669186 reaction equation
Cl[C:2]1[N:3]=[N+:4]([O-:17])[C:5]2[C:14]([N:15]=1)=[CH:13][C:12]1[CH2:11][N:10]([CH3:16])[CH2:9][CH2:8][C:7]=1[CH:6]=2.[CH2:18]([NH2:20])[CH3:19]>COCCOC>[CH2:18]([NH:20][C:2]1[N:3]=[N+:4]([O-:17])[C:5]2[C:14]([N:15]=1)=[CH:13][C:12]1[CH2:11][N:10]([CH3:16])[CH2:9][CH2:8][C:7]=1[CH:6]=2)[CH3:19]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 25139892HCID 25139892, compound

Product 1

HCID 25139025HCID 25139025, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of chloride 257 (500 mg, 2.0 mmol) and ethylamine (0.4 mL, 6.0 mmol) in DME (15 mL) was heated at 60° C. for 4 h in a sealed pressure tube. The solution was cooled to 20° C., the solid filtered off and solvent evaporated. The combined residue was purified by chromatography, eluting with a gradient (2-4%) of MeOH/DCM, to give 1-oxide 258 (460 mg, 88%) as a yellow solid: mp 193-196° C.; 1H NMR δ 8.03 (s, 1H, H-10), 7.27 (s, 1H, H-5), 5.07 (br s, 1H, NH), 3.69 (s, 2H, H-6), 3.53 (dq, J=7.2, 5.8 Hz, 2H, CH2N), 3.05 (t, J=6.0 Hz, 2H, H-8), 2.72 (t, J=6.0 Hz, 2H, H-9), 2.48 (s, 3H, NCH3), 1.29 (t, J=7.2 Hz, 3H, CH3); 13C NMR δ 158.6, 147.0, 144.4, 132.5, 129.6, 122.8, 119.3, 58.2, 52.6, 46.0, 36.3, 29.1, 14.8; MS (APCI) m/z 260 (MH+, 100%). Anal. calcd for C13H17N5O: C, 60.2; H, 6.6; N, 27.0. Found: C, 59.9; H, 6.6; N, 26.9%.

Workup

  1. filtrationthe solid filtered off
  2. customsolvent evaporated
  3. customThe combined residue was purified by chromatography
  4. washeluting with a gradient (2-4%) of MeOH/DCM

Sources & evidence

ORD record
ord-c8af2f4003a5447d8361d77ae6d9a768
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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