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

HRID 1480236Notes

Reaction equation

HRID 1480236 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]([NH2:29])=[O:28])[CH2:23][S:22](=[O:25])(=[O:24])[CH2:21]1>>[NH2:29][C:27](=[O:28])[CH2:26][C:20]1([NH:19][C:10]([C:7]2[CH:6]=[C:5]([O:13][CH2:14][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])[CH2:21][S:22](=[O:24])(=[O:25])[CH2:23]1

Participants

3

Reactant 2

HCID 902036745-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acidHCID 902138302-(3-Amino-1,1-dioxo-thietan-3-yl)acetamide

Product 1

HCID 76281188N-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-5-cyclopropyl-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)acetamide (example 160d) as starting materials and isolated (130 mg, 43%); MS (ESI, m/z): 422.2 (M+H+).

Workup

  1. customisolated (130 mg, 43%)

Sources & evidence

ORD record
ord-c159d2c53ff04bba80884fc2e196f1d3
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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