2-(5-Methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonyl-propan-2-amine → 5-Cyclobutyl-4-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridine-2-carboxylic acid [2-methanesulfonyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

HRID 1480177Notes

Reaction equation

HRID 1480177 reaction equation
[CH:1]1([C:5]2[C:6]([O:14][C@@H:15]([CH3:20])[C:16]([F:19])([F:18])[F:17])=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=2)[CH2:4][CH2:3][CH2:2]1.[CH3:21][S:22]([CH2:25][C:26]([NH2:34])([CH3:33])[C:27]1[N:31]=[C:30]([CH3:32])[O:29][N:28]=1)(=[O:24])=[O:23]>>[CH3:21][S:22]([CH2:25][C:26]([NH:34][C:11]([C:8]1[CH:7]=[C:6]([O:14][C@@H:15]([CH3:20])[C:16]([F:19])([F:18])[F:17])[C:5]([CH:1]2[CH2:2][CH2:3][CH2:4]2)=[CH:10][N:9]=1)=[O:13])([CH3:33])[C:27]1[N:31]=[C:30]([CH3:32])[O:29][N:28]=1)(=[O:23])=[O:24]

Participants

3

Reactant 2

HCID 902034302-(5-Methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonyl-propan-2-amineHCID 902039085-Cyclobutyl-4-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridine-2-carboxylic acid

Product 1

HCID 902035895-Cyclobutyl-4-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridine-2-carboxylic acid [2-methanesulfonyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

Procedure

The title compound was synthesized in analogy to Example 23b, using 5-Cyclobutyl-4-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridine-2-carboxylic acid (Example 110e) and 2-Methanesulfonyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine (Example 109d) as starting materials and isolated (77 mg, 57%) as a white solid; MS (ESI, m/z): 491.6 (M+H+).

Workup

  1. customisolated (77 mg, 57%) as a white solid

Sources & evidence

ORD record
ord-19ba444054bb47c6a40dbd2c203af794
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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