5-Cyclopropyl-4-(2-fluoroethoxy)pyridine-2-carboxylic acid → N-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-5-cyclopropyl-4-(2-fluoroethoxy)pyridine-2-carboxamide

HRID 1480333Notes

Reaction equation

HRID 1480333 reaction equation
[CH:1]1([C:4]2[C:5]([O:13][CH2:14][CH2:15][F:16])=[CH:6][C:7]([C:10]([OH:12])=O)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[NH2:17][C:18]1([CH2:24][C:25]([NH2:27])=[O:26])[CH2:21][S:20](=[O:23])(=[O:22])[CH2:19]1>>[NH2:27][C:25](=[O:26])[CH2:24][C:18]1([NH:17][C:10]([C:7]2[CH:6]=[C:5]([O:13][CH2:14][CH2:15][F:16])[C:4]([CH:1]3[CH2:2][CH2:3]3)=[CH:9][N:8]=2)=[O:12])[CH2:19][S:20](=[O:22])(=[O:23])[CH2:21]1

Participants

3

Reactant 2

HCID 902033525-Cyclopropyl-4-(2-fluoroethoxy)pyridine-2-carboxylic acidHCID 902138302-(3-Amino-1,1-dioxo-thietan-3-yl)acetamide

Product 1

HCID 90215004N-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-5-cyclopropyl-4-(2-fluoroethoxy)pyridine-2-carboxamide

Procedure

The title compound was synthesized in analogy to Example 112e, using 5-cyclopropyl-4-(2-fluoroethoxy)-pyridine-2-carboxylic acid (example 146b) and 2-(3-amino-1,1-dioxo-thietan-3-yl)acetamide (example 160d) as starting materials and isolated (30 mg, 34%); MS (ESI, m/z): 386.2 (M+H+).

Workup

  1. customisolated (30 mg, 34%)

Sources & evidence

ORD record
ord-c2a456313cdb4de599808ae6b6d1c470
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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