5-Cyclobutyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid → N-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-5-cyclobutyl-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxamide

HRID 1480354Notes

Reaction equation

HRID 1480354 reaction equation
[CH: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][CH2:2]1.[NH2:20][C:21]1([CH2:27][C:28]([NH2:30])=[O:29])[CH2:24][S:23](=[O:26])(=[O:25])[CH2:22]1>>[NH2:30][C:28](=[O:29])[CH2:27][C:21]1([NH:20][C:11]([C:8]2[CH:7]=[C:6]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])[C:5]([CH:1]3[CH2:2][CH2:3][CH2:4]3)=[CH:10][N:9]=2)=[O:13])[CH2:22][S:23](=[O:25])(=[O:26])[CH2:24]1

Participants

3

Reactant 2

HCID 902048685-Cyclobutyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acidHCID 902138302-(3-Amino-1,1-dioxo-thietan-3-yl)acetamide

Product 1

HCID 90214963N-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-5-cyclobutyl-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxamide

Procedure

The title compound was synthesized in analogy to Example 112e, using 5-Cyclobutyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (example 108f) and 2-(3-amino-1,1-dioxo-thietan-3-yl)acetamide (example 160d) as starting materials and isolated (16.5 mg, 21%); MS (ESI, m/z): 436.3 (M+H+).

Workup

  1. customisolated (16.5 mg, 21%)

Sources & evidence

ORD record
ord-b7a7d1541e2e422c88ddfb9b7f51403a
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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