Triethylamine → HCID 57914359, compound

HRID 529934Notes

Reaction equation

HRID 529934 reaction equation
[N:1]([CH2:4][CH2:5][NH:6][C:7](=[O:21])[CH2:8][CH2:9][CH2:10][CH2:11]CCCCCCCCC)=[N+:2]=[N-:3].[N:22](CCN)=[N+]=[N-].C(N(CC)CC)C>ClCCl>[N:1]([CH2:4][CH2:5][NH:6][C:7]([C:8]1[NH:22][CH:11]=[CH:10][CH:9]=1)=[O:21])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 55649Ethylamine, 2-azido-HCID 57914356N-(2-azidoethyl)tetradecanamide

Product 1

HCID 57914359HCID 57914359, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in the synthesis of N-(2-azidoethyl)tetradecanamide, (0.249 g, 1.17 mmol) was reacted with 2-azidoethanamine (0.101 g, 1.17 mmol) and triethylamine (0.237 g, 2.34 mmol) in dichloromethane (5 mL) to give N-(2-azidoethyl)-1H-pyrrole-2-carboxamide (0.137 g, 66% yield). 1H NMR (300 MHz, CD3OD) δ 6.88 (d, J=1.5 Hz, 1H), δ 6.77 (d, J=2.4 Hz, 1H), δ 6.14 (t, J=2.4 Hz, 1H), δ 3.46 (t, J=5.7 Hz, 2H), δ 3.37 (q, J=5.7, 14.7 Hz, 2H) ppm; 13C NMR (75 MHz, CD3OD) δ 162.9, 125.6, 122.2, 121.9, 110.9, 109.2, 50.6, 38.9 ppm; HRMS (ESI) calcd for C7H9N5O (M+) 179.0807. found 179.0803.

Sources & evidence

ORD record
ord-b20a33764b7842dda31592ee7c6944d5
Source dataset
uspto-grants-2016_05
Patent number
US09351491B2

Reaction notes

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