Glycolic Acid → n-(2-{2-Ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-ethyl)-2-hydroxy-acetamide

HRID 2037374Notes

Reaction equation

HRID 2037374 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[C:22]([CH3:24])[C:21]([CH2:25][CH:26]([CH3:28])[CH3:27])=[CH:20][N:19]=3)[O:15][N:14]=2)[CH:10]=[C:9]([CH3:29])[C:4]=1[O:5][CH2:6][CH2:7][NH2:8])[CH3:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:61](O)(=[O:64])[CH2:62][OH:63]>C1COCC1.CN(C=O)C>[CH2:1]([C:3]1[CH:12]=[C:11]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[C:22]([CH3:24])[C:21]([CH2:25][CH:26]([CH3:28])[CH3:27])=[CH:20][N:19]=3)[O:15][N:14]=2)[CH:10]=[C:9]([CH3:29])[C:4]=1[O:5][CH2:6][CH2:7][NH:8][C:62](=[O:63])[CH2:61][OH:64])[CH3:2]

Participants

8

Reactant 5

HCID 757Glycolic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 442181592-{2-Ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-ethylamine

Product 1

HCID 44218161n-(2-{2-Ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-ethyl)-2-hydroxy-acetamideYield 55.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound of Example 48 (50 mg, 127 μmol) in THF (2 mL) and DMF (2 mL), EDC hydrochloride (27 mg, 139 μmol), HOBt (19 mg, 139 μmol), DIPEA (25 mg, 190 μmol) and glycolic acid (11 mg, 139 μmol) is added. The mixture is stirred at rt for 1 h before it is concentrated and separated by prep. HPLC to give the title compound (32 mg) as a colourless oil; LC-MS: tR=1.05 min, [M+H]+=453.08; 1H NMR (CDCl): δ1.00 (d, J=6.5 Hz, 6H), 1.31 (t, J=7.3 Hz, 3H), 1.89-2.00 (m, 1H), 2.37 (s, 3H), 2.47 (s, 3H), 2.63 (d, J=7.0 Hz, 2H), 2.73 (q, J=7.5 Hz, 2H), 3.75-3.83 (m, 2H), 3.93-3.99 (m, 2H), 4.23 (s, 2H), 7.03-7.15 (m, 1H), 7.94 (s, 2H), 8.09 (s, 1H), 8.55 (s, 1H).

Workup

  1. concentrationis concentrated
  2. customseparated by prep

Sources & evidence

ORD record
ord-3d6f464e7d2b4ddb96ea8ddadb6e483d
Source dataset
uspto-grants-2013_11
Patent number
US08575200B2

Reaction notes

Loading…