Ethanolamine → 3-{2-ethyl-4-[5-(4-isobutyl-5-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenyl}-N-(2-hydroxy-ethyl)-propionamide

HRID 1676151Notes

Reaction equation

HRID 1676151 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[S:15][C:16]([CH3:23])=[C:17]([CH2:19][CH:20]([CH3:22])[CH3:21])[CH:18]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:24])[C:4]=1[CH2:25][CH2:26][C:27](O)=[O:28])[CH3:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:61]([CH2:63][NH2:64])[OH:62]>C(Cl)Cl.CC(=O)OCC>[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[S:15][C:16]([CH3:23])=[C:17]([CH2:19][CH:20]([CH3:22])[CH3:21])[CH:18]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:24])[C:4]=1[CH2:25][CH2:26][C:27]([NH:64][CH2:63][CH2:61][OH:62])=[O:28])[CH3:2]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 594978783-{2-Ethyl-4-[5-(4-isobutyl-5-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenyl}-propionic acid

Product 1

HCID 237292783-{2-ethyl-4-[5-(4-isobutyl-5-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenyl}-N-(2-hydroxy-ethyl)-propionamideYield 85.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-{2-ethyl-4-[5-(4-isobutyl-5-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenyl}-propionic acid (42 mg, 100 μmol) and DIPEA (39 mg, 300 μmol) in DCM (2 mL), TBTU (32 mg, 100 μmol) followed by ethanolamine (18 mg, 300 μmol) is added. The mixture is stirred at 0° C. for 16 h before it is diluted with EA, washed with 1 N aq. NaOH solution, dried over Na2SO4 and filtered. The solvent is evaporated and the residue is dried under HV to give 3-{2-ethyl-4-[5-(4-isobutyl-5-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenyl}-N-(2-hydroxy-ethyl)-propionamide (39 mg) as a beige solid; LC-MS: tR=1.10 min, [M+1]=456.47.

Workup

  1. additionis added
  2. washwashed with 1 N aq. NaOH solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe solvent is evaporated
  6. customthe residue is dried under HV

Sources & evidence

ORD record
ord-d6f46716531f4c7d8c4d004d6488cc49
Source dataset
uspto-grants-2011_08
Patent number
US08003800B2

Reaction notes

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