N-Methylethylenediamine → HCID 86584214, compound

HRID 1840712Notes

Reaction equation

HRID 1840712 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:26](=[O:27])[C:24]2=[C:25]3[C:20](=[CH:21][CH:22]=[CH:23]2)[C:19](Cl)=[CH:18][CH:17]=[C:16]3[C:14]1=[O:15].[CH3:29][NH:30][CH2:31][CH2:32][NH2:33].C(N(CC)CC)C.C(Cl)(Cl)Cl.CO>COCCO>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:26](=[O:27])[C:24]2=[C:25]3[C:20](=[CH:21][CH:22]=[CH:23]2)[C:19]([NH:33][CH2:32][CH2:31][NH:30][CH3:29])=[CH:18][CH:17]=[C:16]3[C:14]1=[O:15]

Participants

6

Reactant 4

HCID 8014N-MethylethylenediamineHCID 8471TriethylamineHCID 21584188Chloroform methanolHCID 69929180HCID 69929180, compound

Product 1

HCID 86584214HCID 86584214, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

This was prepared analogously to 2ay. The reaction of 1cx (0.613 g, 1.53 mmol), N-methyl-1,2-diaminoethane (0.672 mL, 7.62 mmol), and triethylamine (213 μL, 1.53 mmol) in 2-methoxyethanol, followed by chromatography on silica with a chloroform/methanol gradient, yielded 2cz as a pure yellow powder (0.380 g, 57%). 1H NMR (CDCl3): δ=8.56 (d, 1H, J=7.7 Hz), 8.44 (d, 1H, J=8.4 Hz), 6.16 (d, 1H, J=8.1 Hz), 7.60 (t, 1H, J=7.8 Hz), 6.67 (d, 1H, J=8.4 Hz), 6.25 (br t, 1H, J=4.2 Hz), 4.58 (t, 1H, J=3.6 Hz), 4.16 (t, 2H, J=7.6 Hz), 3.85 (m, 1H), 3.74 (m, 1H), 3.49 (m, 1H), 3.43 (m, 1H), 3.06 (t, 2H, J=5.7 Hz), 2.52 (s, 3H), 1.78-1.66 (m, 6H), 1.53-1.49 (m, 6H). 13C{1H} NMR: δ=164.9, 164.3, 149.8, 134.7, 131.3, 130.0, 126.5, 124.8, 123.3, 120.6, 110.4, 104.6, 98.9, 67.6, 62.4, 49.7, 42.0, 40.3, 36.1, 30.9, 29.7, 28.3, 25.7, 24.1, 19.8. ESI/MS m/z 440 (M+H)+.

Workup

  1. customThis was prepared analogously to 2ay

Sources & evidence

ORD record
ord-4a610a5d079d4d7198d3204223a59293
Source dataset
uspto-grants-2004_01
Patent number
US06682938B1

Reaction notes

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