Ethanolamine → Rac-1-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-3-(2-hydroxy-ethylamino)-propan-2-ol
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][CH:24]([OH:31])[CH2:25]OS(C)(=O)=O)=[CH:19][CH:18]=3)[N:13]=2)=[CH:9][C:8]=1[CH3:32])[CH2:4][CH3:5])[CH3:2].[CH2:33]([CH2:35][NH2:36])[OH:34]>>[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:18]=[CH:19][C:20]([CH2:23][CH:24]([OH:31])[CH2:25][NH:36][CH2:35][CH2:33][OH:34])=[CH:21][CH:22]=3)[N:13]=2)=[CH:9][C:8]=1[CH3:32])[CH2:4][CH3:5])[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
The title compound (16 mg) is prepared starting from rac-methanesulfonic acid 3-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-2-hydroxy-propyl ester (100 mg, 208 μmol) and ethanolamine (64 mg, 1.04 mmol) in analogy to Example 168 step b); LC-MS: tR=0.63 min; [M+1]+=445.07; 1H NMR (CDCl3): δ1.10 (t, J=7.0 Hz, 6H), 2.25 (s, 3H), 2.53 (s br, 2H), 2.59-2.67 (m, 5H), 2.77-2.90 (m, 5H), 3.69 (t, J=5.0 Hz, 2H), 3.72 (s, 2H), 3.95-4.03 (m, 1H), 7.37 (d, J=8.3 Hz, 2H), 7.66 (s, 1H), 8.08 (d, J=8.0 Hz, 2H).
Sources & evidence
- ORD record
- ord-46b4396f4499462fb9029a0320b1fe35
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148410B2
Reaction notes
Loading…