Ethanolamine → 2-((2-(4-(5-(2-Cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)ethyl)amino)ethanol

HRID 2278790Notes

Reaction equation

CS(OC[CH2:7][O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[N:20]=[C:19]([C:21]3[CH:26]=[C:25]([O:27][CH3:28])[N:24]=[C:23]([CH:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)[CH:22]=3)[O:18][N:17]=2)=[CH:11][C:10]=1[CH2:34][CH3:35])(=O)=O.[CH2:36]([CH2:38][NH2:39])[OH:37].[C:40](#N)C>>[CH:29]1([C:23]2[CH:22]=[C:21]([C:19]3[O:18][N:17]=[C:16]([C:12]4[CH:13]=[C:14]([CH3:15])[C:9]([O:8][CH2:7][CH2:40][NH:39][CH2:38][CH2:36][OH:37])=[C:10]([CH2:34][CH3:35])[CH:11]=4)[N:20]=3)[CH:26]=[C:25]([O:27][CH3:28])[N:24]=2)[CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

Reactant 3

HCID 700Ethanolamine

HCID 6342Acetonitrile

HCID 867020182-(4-(5-(2-Cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)ethyl methanesulfonate

Product 1

HCID 575247042-((2-(4-(5-(2-Cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)ethyl)amino)ethanol

Conditions

Temperature: 65 °C

Procedure

A mixture of 2-(4-(5-(2-cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenoxy)ethyl methanesulfonate (184 mg, 0.367 mmol) and ethanolamine (112 mg, 1.83 mmol) in acetonitrile (6 mL) is stirred at 65° C. for 18 h before it is separated by prep. HPLC to give the title compound (77 mg) as a white solid; LC-MS: tR=0.92 min, [M+H]+=467.25; 1H NMR (CD3OD): δ 7.91 (s, 1H), 7.88 (s, 1H), 7.62 (s, 1H), 7.41 (s, 1H), 4.20 (t, J=5.0 Hz, 2H), 4.07 (s, 3H), 3.93 (t, J=5.1 Hz, 2H), 3.60 (t, J=4.9 Hz, 2H), 3.34-3.38 (m, 2H), 3.24-3.31 (m, 1H), 2.82 (q, J=7.5 Hz, 2H), 2.45 (s, 3H), 2.10-2.19 (m, 2H), 1.85-1.97 (m, 4H), 1.72-1.84 (m, 2H), 1.35 (t, J=7.5 Hz, 3H).

Workup

customis separated by prep

Sources & evidence

ORD record: ord-9dcf07f6081b4fcdb694d3fd76037fd4
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133179B2

Reaction notes

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