Triethylamine → {3-[3-(tert-butoxycarbonyl-cyclopropylmethyl-amino)-propylamino]-2-oxo-2H-pyrazin-1-yl}-acetic acid ethyl ester

HRID 1795295Notes

Reaction equation

HRID 1795295 reaction equation
[C:1]([O:5][C:6](=[O:16])[N:7]([CH2:12][CH2:13][CH2:14][NH2:15])[CH2:8][CH:9]1[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[CH2:17]([O:19][C:20](=[O:30])[CH2:21][N:22]1[CH:27]=[CH:26][N:25]=[C:24](Br)[C:23]1=[O:29])[CH3:18].C(N(CC)CC)C>C(O)C>[CH2:17]([O:19][C:20](=[O:30])[CH2:21][N:22]1[CH:27]=[CH:26][N:25]=[C:24]([NH:15][CH2:14][CH2:13][CH2:12][N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:16])[CH2:8][CH:9]2[CH2:10][CH2:11]2)[C:23]1=[O:29])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11807445(3-Bromo-2-oxo-2H-pyrazin-1-yl)-acetic Acid Ethyl EsterHCID 21023634(3-Amino-propyl)-cyclopropylmethyl-carbamic acid tert-butyl ester

Product 1

HCID 21023630{3-[3-(tert-butoxycarbonyl-cyclopropylmethyl-amino)-propylamino]-2-oxo-2H-pyrazin-1-yl}-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (3-amino-propyl)-cyclopropylmethyl-carbamic acid tert-butyl ester (5 g, 0.022 mol), (3-bromo-2-oxo-2H-pyrazin-1-yl)-acetic acid ethyl ester (5.2 g, 0.020 mol, preparation described in example 17, step J) and triethylamine (3.3 ml, 0.024 mol) in ethanol (16 ml) was heated to 80° C. in a sealed tube overnight. Concentration and flash chromatography (silica gel, chloroform-diethyl ether, 90: 10) gave {3-[3-(tert-butoxycarbonyl-cyclopropylmethyl-amino)-propylamino]-2-oxo-2H-pyrazin-1-yl}-acetic acid ethyl ester; 1H NMR (CDCl3, 400 MHz) δ 6.85 (d, 1H, J=4.7 Hz), 6.36 (d, 1H, J=4.7 Hz), 4.56 (s, 2H), 4.25 (q, 2H, J=7.1 Hz), 3.42 (m, 2H), 3.36 (m, 2H), 3.10 (m, 2H), 1.87 (m, 2H), 1.46 (s, 9H), 1.30 (t, 3H, J=7.1 Hz), 0.96 (m, 1H), 0.48 (m, 2H), 0.20 (m, 2H).

Workup

  1. concentrationConcentration and flash chromatography (silica gel, chloroform-diethyl ether, 90: 10)

Sources & evidence

ORD record
ord-c103034f46aa426bae9c25608e9f6fa7
Source dataset
uspto-grants-2006_04
Patent number
US07026324B2

Reaction notes

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