3,3-Difluoroazetidine hydrochloride → 5-cyclopropyl-N-[1-(3,3-difluoroazetidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl]-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide

HRID 1480278Notes

Reaction equation

HRID 1480278 reaction equation
[CH:1]1([C:4]2[C:5]([O:21][C@@H:22]([CH3:27])[C:23]([F:26])([F:25])[F:24])=[CH:6][C:7]([C:10]([NH:12][CH:13]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:14]([OH:16])=O)=[O:11])=[N:8][CH:9]=2)[CH2:3][CH2:2]1.Cl.[F:29][C:30]1([F:34])[CH2:33][NH:32][CH2:31]1>>[CH:1]1([C:4]2[C:5]([O:21][C@@H:22]([CH3:27])[C:23]([F:25])([F:26])[F:24])=[CH:6][C:7]([C:10]([NH:12][CH:13]([C:17]([CH3:18])([CH3:19])[CH3:20])[C:14]([N:32]3[CH2:33][C:30]([F:34])([F:29])[CH2:31]3)=[O:16])=[O:11])=[N:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 27582473,3-Difluoroazetidine hydrochlorideHCID 902035392-[[5-cyclopropyl-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carbonyl]amino]-3,3-dimethyl-butanoic acid

Product 1

HCID 902043785-cyclopropyl-N-[1-(3,3-difluoroazetidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl]-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxypyridine-2-carboxamide

Procedure

The title compound was synthesized in analogy to Example 112e, using 2-[[5-cyclopropyl-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carbonyl]amino]-3,3-dimethyl-butanoic acid (Example 199b) and 3,3-Difluoroazetidine hydrochloride (CAN 288315-03-7) as starting materials and isolated (35 mg, 58%); MS (ESI, m/z): 464.6 (M+H+).

Workup

  1. customisolated (35 mg, 58%)

Sources & evidence

ORD record
ord-ab8d8e2b6be54b93a7aebeabb35016b5
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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