N-(2-aminoethyl)-N-ethyl-N-[2-(2-nitropyridin-3-yloxy)ethyl]amine → Tert-butyl N-[2-[N-ethyl-N-[2-(2-nitropyridin-3-yloxy)ethyl]amino]ethyl]carbamate

HRID 2273644Notes

Reaction equation

HRID 2273644 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH2:17][CH3:18])[CH2:5][CH2:6][O:7][C:8]1[C:9]([N+:14]([O-:16])=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=1.C(N(CCN[C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])CCOC1C(F)=NC=CC=1)C>>[CH2:17]([N:4]([CH2:3][CH2:2][NH:1][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:5][CH2:6][O:7][C:8]1[C:9]([N+:14]([O-:16])=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:18]

Participants

3

Reactant 2

HCID 52952580N-(2-aminoethyl)-N-ethyl-N-[2-(2-nitropyridin-3-yloxy)ethyl]amineHCID 52952582Tert-butyl N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]carbamate

Product 1

HCID 52952685Tert-butyl N-[2-[N-ethyl-N-[2-(2-nitropyridin-3-yloxy)ethyl]amino]ethyl]carbamateYield 64%

Procedure

This compound was prepared, starting from compound 59 (500 mg, 1.97 mmol), according to the procedure developed for compound 64. Reaction time at room temperature: 18 h to give compound 65 (444 mg, 1.25 mmol) as a yellow oil. Yield 64%; IR (CCl4) ν 1172, 1289, 1367, 1500, 1549, 1716, 2977 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.00 (t, 3H, J=7.1 Hz), 1.36 (s, 9H), 2.60 (m, 4H), 2.89 (t, 2H, J=5.6 Hz), 3.13 (q, 2H, J=5.9 Hz), 4.13 (t, 2H, J=5.6 Hz), 7.51 (m, 2H), 8.05 (dd, 1H, J=2.4, 3.4 Hz); ESI-MS m/z 355.1 [M+H]+.

Workup

  1. customThis compound was prepared
  2. customReaction time at room temperature

Sources & evidence

ORD record
ord-d25a6c037ed44f96957f1e213c7fa572
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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