Ethanolamine → HCID 67265471, compound

HRID 1685764Notes

Reaction equation

[CH2:1]([N:3]([CH2:6][C:7]1[S:11][C:10]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24]OS(C)(=O)=O)=[CH:19][CH:18]=3)[N:13]=2)=[CH:9][C:8]=1[CH3:30])[CH2:4][CH3:5])[CH3:2].[CH2:31]([CH2:33][NH2:34])[OH:32]>>[CH2:1]([N:3]([CH2:6][C:7]1[S:11][C:10]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][NH:34][CH2:33][CH2:31][OH:32])=[CH:19][CH:18]=3)[N:13]=2)=[CH:9][C:8]=1[CH3:30])[CH2:4][CH3:5])[CH3:2]

Participants

Reactant 2

HCID 700Ethanolamine

HCID 86646455HCID 86646455, compound

Product 1

HCID 67265471HCID 67265471, compoundYield 13%

Procedure

The title compound (6 mg) is prepared in analogy to Example 160 starting from methanesulfonic acid 2-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethyl ester (50 mg, 111 μmol) and ethanolamine (34 mg, 556 μmol); LC-MS: tR=0.63 min; [M+1]+=415.07; 1H NMR (CDCl3): δ1.11 (t, J=7.0 Hz, 6H), 2.26 (s, 3H), 2.63 (q, J=7.0 Hz, 4H), 2.80-2.86 (m, 2H), 2.87-2.93 (m, 2H), 2.94-3.00 (m, 2H), 3.62-3.67 (m, 2H), 3.73 (s, 2H), 7.35 (d, J=8.0 Hz, 2H), 7.67 (s, 1H), 8.09 (d, J=8.0 Hz, 2H).

Sources & evidence

ORD record: ord-f548f740d3cc4e41bc6418c9e6abf7fe
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148410B2

Reaction notes

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