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

HRID 2065921Notes

Reaction equation

HRID 2065921 reaction equation
[CH2:1]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23](O)=[O:24])=[CH:18][CH:17]=3)[N:12]=2)=[CH:7][C:6]=1[CH3:26])[CH:2]([CH3:4])[CH3:3].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH2:58]([CH2:60][NH2:61])[OH:59]>CN(C=O)C.CC(=O)OCC>[OH:59][CH2:58][CH2:60][NH:61][C:23](=[O:24])[CH2:22][C:19]1[CH:20]=[CH:21][C:16]([C:13]2[N:12]=[C:11]([C:8]3[CH:9]=[N:10][C:5]([CH2:1][CH:2]([CH3:3])[CH3:4])=[C:6]([CH3:26])[CH:7]=3)[O:15][N:14]=2)=[CH:17][CH:18]=1

Participants

8

Reactant 5

HCID 700EthanolamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59392514{4-[5-(6-Isobutyl-5-methyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-acetic acid

Product 1

HCID 59392517N-(2-hydroxy-ethyl)-2-{4-[5-(6-isobutyl-5-methyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-acetamideYield 46.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of {4-[5-(6-isobutyl-5-methyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-acetic acid (50 mg, 142 μmol) in DMF (3 mL), EDC HCl (33 mg, 171 μmol), HOBt (23 mg, 171 μmol) and DIPEA (28 mg, 213 μmol) is added. The mixture is stirred at rt for 5 min before ethanolamine (10 mg, 157 μmol) is added. Stirring is continued at rt for 72 h. The mixture is diluted with EA, washed with water, and concentrated. The crude product is purified on prep. TLC plates with DCM containing 10% of MeOH to give N-(2-hydroxy-ethyl)-2-{4-[5-(6-isobutyl-5-methyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-acetamide (26 mg) as a white solid; LC-MS: tR=0.82 min, [M+1]+=395.15; 1H NMR (CDCl3): δ1.01 (d, J=6.5 Hz, 6H), 2.19-2.29 (m, 1H), 2.46 (s, 3H), 2.53 (s br, 1H), 2.80 (d, J=7.3 Hz, 2H), 3.44 (q, J=4.8 Hz, 2H), 3.69 (s, 2H), 3.71-3.75 (m, 2H), 5.96 (s br, 1H), 7.46 (d, J=7.5 Hz, 2H), 8.18 (d, J=7.8 Hz, 2H), 8.17 (s), 8.19 (s), 8.22 (s, 1H), 9.20 (s, 1H).

Workup

  1. additionis added
  2. washwashed with water
  3. concentrationconcentrated
  4. customThe crude product is purified on prep

Sources & evidence

ORD record
ord-da1795dc45db42f484f4c000eb543b06
Source dataset
uspto-grants-2012_10
Patent number
US08288554B2

Reaction notes

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