Triethylamine → 1-(2-Hex-5-ynoylperhydropyridazinyl)-3,3-dimethylpentane-1,2-dione

HRID 851947

Reaction equation

[C:1](O)(=[O:7])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH3:24][C:25]([CH3:38])([CH2:36][CH3:37])[C:26](=[O:35])[C:27]([CH:29]1[CH2:34][CH2:33][CH2:32][NH:31][NH:30]1)=[O:28]>>[C:1]([N:30]1[CH:29]([C:27](=[O:28])[C:26](=[O:35])[C:25]([CH3:38])([CH3:24])[CH2:36][CH3:37])[CH2:34][CH2:33][CH2:32][NH:31]1)(=[O:7])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6]

Participants

Reactant 4

HCID 8471Triethylamine

HCID 62365Isobutyl chloroformate

HCID 1430365-Hexynoic acid

HCID 694178043,3-Dimethyl-1-perhydropyridazinylpentane-1,2-dione

Product 1

HCID 184700651-(2-Hex-5-ynoylperhydropyridazinyl)-3,3-dimethylpentane-1,2-dioneYield 63%

Procedure

To a solution of 5-hexynoic acid (0.467 g, 4 mmol) in 10 ml CH2Cl2was added triethylamine (0.56 ml, 4 mmol), followed by isobutyl chloroformate (0.53 ml, 4 mmol) at 0° C. After stirring for 5 minutes, a solution of 3,3-dimethyl-1-perhydropyridazinyl pentane-1,2-dione (0.424 g, 2 mmol) in 1 ml CH2Cl2was added. The reaction was gradually warmed up to room temperature. The crude material was subject to silica gel purification to yield final product as clear oil (0.385 g, 63%). 1H NMR (CDCl3, 400 MHz): δ 0.91 (t, 3H, J=7.0); 1.26 (s, 6H); 1.76(m, 8H); 2.28 (m, 2H); 2.50 (m, 2H); 2.88 (m, 2H); 3.60 (m, 1H); 4.50 (m, 2H).

Workup

customThe crude material was subject to silica gel purification

Sources & evidence

ORD record: ord-31834923f74a48afa743f4d505a429d9
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253169B2

Linked notes

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