5-(1-Fluorocyclobutyl)-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxylic acid → N-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-5-(1-fluorocyclobutyl)-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxamide

HRID 1480339Notes

Reaction equation

HRID 1480339 reaction equation
[F:1][C:2]1([C:6]2[C:7]([O:15][CH2:16][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.[NH2:21][C:22]1([CH2:28][C:29]([NH2:31])=[O:30])[CH2:25][S:24](=[O:27])(=[O:26])[CH2:23]1>>[NH2:31][C:29](=[O:30])[CH2:28][C:22]1([NH:21][C:12]([C:9]2[CH:8]=[C:7]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])[C:6]([C:2]3([F:1])[CH2:3][CH2:4][CH2:5]3)=[CH:11][N:10]=2)=[O:14])[CH2:23][S:24](=[O:26])(=[O:27])[CH2:25]1

Participants

3

Reactant 2

HCID 902034925-(1-Fluorocyclobutyl)-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxylic acidHCID 902138302-(3-Amino-1,1-dioxo-thietan-3-yl)acetamide

Product 1

HCID 90214990N-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-5-(1-fluorocyclobutyl)-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxamide

Procedure

The title compound was synthesized in analogy to Example 112e, using 5-(1-fluorocyclobutyl)-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxylic acid (example 285a) and 2-(3-amino-1,1-dioxo-thietan-3-yl)acetamide (example 160d) as starting materials and isolated (16 mg, 21%); MS (ESI, m/z): 454.3 (M+H+).

Workup

  1. customisolated (16 mg, 21%)

Sources & evidence

ORD record
ord-528e317d9bc54f07bee1cc79bb862e52
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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