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

HRID 1480328Notes

Reaction equation

HRID 1480328 reaction equation
[CH:1]1([C:4]2[C:5]([O:13][CH2:14][CH:15]([F:17])[F:16])=[CH:6][C:7]([C:10]([OH:12])=O)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[NH2:18][C:19]1([CH2:25][C:26]([NH2:28])=[O:27])[CH2:22][S:21](=[O:24])(=[O:23])[CH2:20]1>>[NH2:28][C:26](=[O:27])[CH2:25][C:19]1([NH:18][C:10]([C:7]2[CH:6]=[C:5]([O:13][CH2:14][CH:15]([F:17])[F:16])[C:4]([CH:1]3[CH2:2][CH2:3]3)=[CH:9][N:8]=2)=[O:12])[CH2:20][S:21](=[O:23])(=[O:24])[CH2:22]1

Participants

3

Reactant 2

HCID 902035305-Cyclopropyl-4-(2,2-difluoroethoxy)pyridine-2-carboxylic acidHCID 902138302-(3-Amino-1,1-dioxo-thietan-3-yl)acetamide

Product 1

HCID 90214988N-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-5-cyclopropyl-4-(2,2-difluoroethoxy)pyridine-2-carboxamide

Procedure

The title compound was synthesized in analogy to Example 112e, using 5-cyclopropyl-4-(2,2-difluoroethoxy)pyridine-2-carboxylic acid (example 145d) and 2-(3-amino-1,1-dioxo-thietan-3-yl)acetamide (example 160d) as starting materials and isolated (51 mg, 59%); MS (ESI, m/z): 404.3 (M+H+).

Workup

  1. customisolated (51 mg, 59%)

Sources & evidence

ORD record
ord-395fda69e26b45828be35cc277ec63bc
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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