HCID 25069533, compound → HCID 25074253, compound

HRID 2047317Notes

Reaction equation

HRID 2047317 reaction equation
[CH2:1]([N:3]([CH2:35][CH3:36])[C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:30]=[C:29]([CH3:31])[C:18]([O:19][CH2:20][C@H:21]([OH:28])[CH2:22][NH:23][C:24](=[O:27])[CH2:25][OH:26])=[C:17]([CH2:32][CH3:33])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:34])[N:5]=1)[CH3:2].NC[C@H](O)COC1C(C)=CC(C2N=C(C3C=C(C)N=C(N(CC)CC)C=3)ON=2)=CC=1CC>>[CH2:35]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:30]=[C:29]([CH3:31])[C:18]([O:19][CH2:20][C@@H:21]([OH:28])[CH2:22][NH:23][C:24](=[O:27])[CH2:25][OH:26])=[C:17]([CH2:32][CH3:33])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:34])[N:5]=1)[CH3:36]

Participants

3

Reactant 2

HCID 25069533HCID 25069533, compoundHCID 68578392HCID 68578392, compound

Product 1

HCID 25074253HCID 25074253, compound

Procedure

N-(3-{4-[5-(2-Diethylamino-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-(S)-2-hydroxy-propyl)-2-hydroxy-acetamide is prepared in analogy to N-(3-{4-[5-(2-diethylamino-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-(R)-2-hydroxy-propyl)-2-hydroxy-acetamide starting from (S)-1-amino-3-{4-[5-(2-diethylamino-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propan-2-ol; LC-MS: tR=0.78 min; [M+1]+=498.20; 1H NMR (CDCl3): δ 1.24 (t, J=7.0 Hz, 6H), 1.32 (t, J=7.3 Hz, 3H), 2.39 (s, 3H), 2.49 (s, 3H), 2.75 (q, J=7.5 Hz, 2H), 2.83 (s br, 1H), 3.44 (s br, 1H), 3.48-3.57 (m, 1H), 3.62 (q, J=6.8 Hz, 4H), 3.75-3.94 (m, 3H), 4.17-4.25 (m, 3H), 7.00 (s, 1H), 7.05 (t, J=4.5 Hz, 1H), 7.09 (s, 1H), 7.87 (s, 1H), 7.88 (s, 1H).

Sources & evidence

ORD record
ord-70a443cc5a734ea181879dc1dcdbe748
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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