4-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid → N-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-4-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide

HRID 1480321Notes

Reaction equation

HRID 1480321 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:11]([N:12]3[CH2:15][C:14]([F:17])([F:16])[CH2:13]3)=[CH:10][N:9]=[C:8]([C:18]([OH:20])=O)[CH:7]=2)[CH2:3][CH2:2]1.[NH2:21][C:22]1([CH2:28][C:29]([NH2:31])=[O:30])[CH2:25][S:24](=[O:27])(=[O:26])[CH2:23]1>>[NH2:31][C:29](=[O:30])[CH2:28][C:22]1([NH:21][C:18]([C:8]2[CH:7]=[C:6]([O:5][CH2:4][CH:1]3[CH2:2][CH2:3]3)[C:11]([N:12]3[CH2:13][C:14]([F:16])([F:17])[CH2:15]3)=[CH:10][N:9]=2)=[O:20])[CH2:23][S:24](=[O:26])(=[O:27])[CH2:25]1

Participants

3

Reactant 2

HCID 902040914-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acidHCID 902138302-(3-Amino-1,1-dioxo-thietan-3-yl)acetamide

Product 1

HCID 90204435N-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-4-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide

Procedure

The title compound was synthesized in analogy to Example 112e, using 4-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (example 53e) and 2-(3-amino-1,1-dioxo-thietan-3-yl)acetamide (example 160d) as starting materials and isolated (35 mg, 42%); MS (ESI, m/z): 445.3 (M+H+).

Workup

  1. customisolated (35 mg, 42%)

Sources & evidence

ORD record
ord-0c3854c5b109495197ff17bb88a42c46
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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