2-(5-Methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonyl-propan-2-amine → 5-(1-hydroxycyclobutyl)-N-[1-methyl-1-(5-methyl-1,2,4-oxadiazol-3-yl)-2-methylsulfonyl-ethyl]-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carboxamide

HRID 1480194Notes

Reaction equation

HRID 1480194 reaction equation
[OH:1][C:2]1([C:6]2[C:7]([O:15][C@@H:16]([CH3:21])[C:17]([F:20])([F:19])[F:18])=[CH:8][C:9]([C:12]([OH:14])=O)=[N:10][CH:11]=2)[CH2:5][CH2:4][CH2:3]1.[CH3:22][S:23]([CH2:26][C:27]([NH2:35])([CH3:34])[C:28]1[N:32]=[C:31]([CH3:33])[O:30][N:29]=1)(=[O:25])=[O:24]>>[OH:1][C:2]1([C:6]2[C:7]([O:15][C@@H:16]([CH3:21])[C:17]([F:19])([F:20])[F:18])=[CH:8][C:9]([C:12]([NH:35][C:27]([C:28]3[N:32]=[C:31]([CH3:33])[O:30][N:29]=3)([CH3:34])[CH2:26][S:23]([CH3:22])(=[O:25])=[O:24])=[O:14])=[N:10][CH:11]=2)[CH2:5][CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 902034302-(5-Methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonyl-propan-2-amineHCID 902040375-(1-hydroxycyclobutyl)-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carboxylic acid

Product 1

HCID 902034235-(1-hydroxycyclobutyl)-N-[1-methyl-1-(5-methyl-1,2,4-oxadiazol-3-yl)-2-methylsulfonyl-ethyl]-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carboxamide

Procedure

The title compound was synthesized in analogy to Example 112e, using 5-(1-hydroxycyclobutyl)-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carboxylic acid (Example 126d) and 2-Methanesulfonyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine (example 109d) as starting materials and isolated (28 mg, 42%); MS (ESI, m/z): 507.5 (M+H+).

Workup

  1. customisolated (28 mg, 42%)

Sources & evidence

ORD record
ord-1aa6d3e782c8461bb8b61797c1ee6720
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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