3-Bromo-1-propanol → 2-((3-(4-(3-(2-Cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-5-yl)-2-ethyl-6-methylphenoxy)propyl)amino)acetic acid

HRID 2278807Notes

Reaction equation

HRID 2278807 reaction equation
[CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[N:16]=[C:15]([C:17]4[CH:22]=[C:21]([CH3:23])[C:20]([OH:24])=[C:19]([CH2:25][CH3:26])[CH:18]=4)[O:14][N:13]=3)[CH:9]=[C:8]([O:27][CH3:28])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:30][CH2:31][CH2:32]O.C([O:38][C:39](=[O:42])[CH2:40][NH2:41])(C)(C)C>>[CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[N:16]=[C:15]([C:17]4[CH:22]=[C:21]([CH3:23])[C:20]([O:24][CH2:30][CH2:31][CH2:32][NH:41][CH2:40][C:39]([OH:38])=[O:42])=[C:19]([CH2:25][CH3:26])[CH:18]=4)[O:14][N:13]=3)[CH:9]=[C:8]([O:27][CH3:28])[N:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 123083-Bromo-1-propanolHCID 151417Glycine tert-butyl esterHCID 1363910174-[3-(2-Cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-5-yl]-2-ethyl-6-methyl-phenol

Product 1

HCID 575203912-((3-(4-(3-(2-Cyclopentyl-6-methoxypyridin-4-yl)-1,2,4-oxadiazol-5-yl)-2-ethyl-6-methylphenoxy)propyl)amino)acetic acid

Procedure

The title compound is prepared starting from 4-[3-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-5-yl]-2-ethyl-6-methyl-phenol (Example 53, step b) in analogy to Example 1 using 3-bromo-propanol and glycine tert.-butyl ester; LC-MS: tR=0.97 min, [M+H]+=495.24; 1H NMR (CDCl3): δ 7.84 (s, 1H), 7.80 (s, 1H), 7.41 (s, 1H), 7.22 (s, 1H), 3.97 (s, 3H), 3.91 (t, J=5.3 Hz, 2H), 3.66 (s, 2H), 3.34-3.41 (m, 2H), 3.13-3.23 (m, 1H), 2.68 (q, J=7.4 Hz, 2H), 2.35-2.43 (m, 2H), 2.33 (s, 3H), 2.02-2.11 (m, 2H), 1.81-1.93 (m, 4H), 1.67-1.76 (m, 2H), 1.29 (t, J=7.5 Hz, 3H); 13C NMR (CDCl3): δ 175.7, 170.8, 167.7, 165.0, 164.2, 158.8, 137.9, 136.7, 131.9, 129.0, 127.3, 120.0, 111.9, 105.5, 70.0, 53.5, 50.0, 47.5, 45.4, 33.3, 27.2, 25.9, 22.8, 16.5, 14.7.

Sources & evidence

ORD record
ord-246ea5bd29b44c3182ac6b4c68268df9
Source dataset
uspto-grants-2015_09
Patent number
US09133179B2

Reaction notes

Loading…