2-(5-Methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonyl-propan-2-amine → 5-(cyclobuten-1-yl)-N-[2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonylpropan-2-yl]-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxamide

HRID 1480198Notes

Reaction equation

HRID 1480198 reaction equation
[C:1]1([C:5]2[C:6]([O:14][CH2:15][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][CH:2]=1.[CH3:20][S:21]([CH2:24][C:25]([NH2:33])([CH3:32])[C:26]1[N:30]=[C:29]([CH3:31])[O:28][N:27]=1)(=[O:23])=[O:22]>>[C:1]1([C:5]2[C:6]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:7][C:8]([C:11]([NH:33][C:25]([C:26]3[N:30]=[C:29]([CH3:31])[O:28][N:27]=3)([CH3:32])[CH2:24][S:21]([CH3:20])(=[O:23])=[O:22])=[O:13])=[N:9][CH:10]=2)[CH2:4][CH2:3][CH:2]=1

Participants

3

Reactant 2

HCID 902034302-(5-Methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonyl-propan-2-amineHCID 902043875-(Cyclobuten-1-yl)-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxylic acid

Product 1

HCID 902044345-(cyclobuten-1-yl)-N-[2-(5-methyl-1,2,4-oxadiazol-3-yl)-1-methylsulfonylpropan-2-yl]-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxamide

Procedure

The title compound was synthesized in analogy to Example 112e, using 5-(cyclobuten-1-yl)-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxylic acid (Example 127d) and 2-Methanesulfonyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine (example 109d) as starting materials and isolated (25 mg, 14%); MS (ESI, m/z): 475.5 (M+H+).

Workup

  1. customisolated (25 mg, 14%)

Sources & evidence

ORD record
ord-02beded38aaa4da2b90f23807505ae45
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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