5-Cyclopropyl-4-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridine-2-carboxylic acid → N-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-5-cyclopropyl-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide

HRID 1480320Notes

Reaction equation

HRID 1480320 reaction equation
[CH:1]1([C:4]2[C:5]([O:13][C@@H:14]([CH3:19])[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.[NH2:20][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:10]([C:7]2[CH:6]=[C:5]([O:13][C@@H:14]([CH3:19])[C:15]([F:18])([F:17])[F:16])[C:4]([CH:1]3[CH2:2][CH2:3]3)=[CH:9][N:8]=2)=[O:12])[CH2:22][S:23](=[O:25])(=[O:26])[CH2:24]1

Participants

3

Reactant 2

HCID 902045735-Cyclopropyl-4-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridine-2-carboxylic acidHCID 902138302-(3-Amino-1,1-dioxo-thietan-3-yl)acetamide

Product 1

HCID 90214979N-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-5-cyclopropyl-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide

Procedure

The title compound was synthesized in analogy to Example 112e, using 5-Cyclopropyl-4-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-pyridine-2-carboxylic acid (example 68a) and 2-(3-amino-1,1-dioxo-thietan-3-yl)acetamide (example 160d) as starting materials and isolated (19.3 mg, 28%); MS (ESI, m/z): 436.3 (M+H+).

Workup

  1. customisolated (19.3 mg, 28%)

Sources & evidence

ORD record
ord-37747f01d844450cbdcad9255b6813b3
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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