5-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid → 5-cyclopropyl-N-[3-[2-(methylamino)-2-oxoethyl]-1,1-dioxothietan-3-yl]-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxamide

HRID 1480335Notes

Reaction equation

HRID 1480335 reaction equation
[CH:1]1([C:4]2[C:5]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:6][C:7]([C:10]([OH:12])=O)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[NH2:19][C:20]1([CH2:26][C:27]([NH:29][CH3:30])=[O:28])[CH2:23][S:22](=[O:25])(=[O:24])[CH2:21]1>>[CH:1]1([C:4]2[C:5]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:6][C:7]([C:10]([NH:19][C:20]3([CH2:26][C:27]([NH:29][CH3:30])=[O:28])[CH2:23][S:22](=[O:25])(=[O:24])[CH2:21]3)=[O:12])=[N:8][CH:9]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 902036745-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acidHCID 902149512-(3-amino-1,1-dioxo-thietan-3-yl)-N-methyl-acetamide

Product 1

HCID 902149915-cyclopropyl-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-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (example 48c) and 2-(3-amino-1,1-dioxo-thietan-3-yl)-N-methyl-acetamide (example 282a) as starting materials and isolated (56 mg, 76%); MS (ESI, m/z): 436.3 (M+H+).

Workup

  1. customisolated (56 mg, 76%)

Sources & evidence

ORD record
ord-95d33ce38d1d4fa6ba83a6556614d476
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

Loading…