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

HRID 1480338Notes

Reaction equation

HRID 1480338 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]([NH:31][CH3:32])=[O:30])[CH2:25][S:24](=[O:27])(=[O:26])[CH2:23]1>>[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]([NH:21][C:22]3([CH2:28][C:29]([NH:31][CH3:32])=[O:30])[CH2:25][S:24](=[O:27])(=[O:26])[CH2:23]3)=[O:14])=[N:10][CH:11]=2)[CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 902034925-(1-Fluorocyclobutyl)-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxylic acidHCID 902149512-(3-amino-1,1-dioxo-thietan-3-yl)-N-methyl-acetamide

Product 1

HCID 902149535-(1-fluorocyclobutyl)-N-[3-[2-(methylamino)-2-oxoethyl]-1,1-dioxothietan-3-yl]-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)-N-methyl-acetamide (example 282a) as starting materials and isolated (15 mg, 19%); MS (ESI, m/z): 468.3 (M+H+).

Workup

  1. customisolated (15 mg, 19%)

Sources & evidence

ORD record
ord-104d6269c3df417ebb5484c7d655b1b5
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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