Ethylamine → 1-(3-Methyl-butyl)-4-nitro-1H-pyrrole-2-carboxylic acid [2-(N,N'-diethylcarbamimidoyl)-ethyl]-amide

HRID 23157Notes

Reaction equation

HRID 23157 reaction equation
[C:1](CC[NH-])#N.[CH3:6][NH:7][C:8]([CH2:11][CH2:12][NH:13][C:14]([C:16]1[N:17]([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[CH:20]=1)=[O:15])=NC.[CH2:29]([NH2:31])[CH3:30]>>[CH2:29]([NH:31][C:8]([CH2:11][CH2:12][NH:13][C:14]([C:16]1[N:17]([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[CH:20]=1)=[O:15])=[N:7][CH2:6][CH3:1])[CH3:30]

Participants

4

Reactant 3

HCID 6341EthylamineHCID 11141857HCID 11141857, compoundHCID 86584756Cyanoethylamide

Product 1

HCID 865847551-(3-Methyl-butyl)-4-nitro-1H-pyrrole-2-carboxylic acid [2-(N,N'-diethylcarbamimidoyl)-ethyl]-amide

Procedure

Compound 272 was synthesized from cyanoethylamide 242 as described above for compound 270 using ethylamine (3 ml). ES MS: 351.53. (M+H+). H1-NMR (DMSO-d6): 0.86-0.88 (d, 6H, CH3-isopentyl), 1.07-1.17 (t, 6H, CH3-ethyl), 1.42-1.60 (m, 3H, CH & CH2—CH), 2.67-2.72 (t, 2H, CH2 CH2-amidine), 3.12-3.21 (m, 2H, CH2-ethyl), 3.36-3.50 (m, 4H, CH2—NHCO and CH2-ethyl), 4.33-4.38 (t, 2H, CH3—N), 7.39 and 8.20 (d, 1H, pyrrole), 8.63-8.71 (NH-amidine), 9.30 (t, 1H, NHCO).

Sources & evidence

ORD record
ord-5d708b24ccee4ada8f0c283eb8ea3dbf
Source dataset
uspto-grants-2005_02
Patent number
US06849713B2

Reaction notes

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