3,3-Difluoroazetidine hydrochloride → 6-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid [(S)-1-(3,3-difluoro-azetidine-1-carbonyl)-2,2-dimethyl-propyl]-amide

HRID 927761Notes

Reaction equation

HRID 927761 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([NH:14][C@@H:15]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:16](O)=[O:17])=[O:13])[CH:9]=[CH:8][C:7]=2[N:23]2[CH2:26][C:25]([F:28])([F:27])[CH2:24]2)[CH2:3][CH2:2]1.Cl.[F:30][C:31]1([F:35])[CH2:34][NH:33][CH2:32]1>>[F:30][C:31]1([F:35])[CH2:34][N:33]([C:16]([C@@H:15]([NH:14][C:12]([C:10]2[CH:9]=[CH:8][C:7]([N:23]3[CH2:26][C:25]([F:28])([F:27])[CH2:24]3)=[C:6]([O:5][CH2:4][CH:1]3[CH2:3][CH2:2]3)[N:11]=2)=[O:13])[C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])[CH2:32]1

Participants

3

Reactant 2

HCID 27582473,3-Difluoroazetidine hydrochlorideHCID 71087773(S)-2-(6-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinamido)-3,3-dimethylbutanoic acid

Product 1

HCID 711056956-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid [(S)-1-(3,3-difluoro-azetidine-1-carbonyl)-2,2-dimethyl-propyl]-amide

Procedure

The title compound was synthesized in analogy to Example 1, using (S)-2-(6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinamido)-3,3-dimethylbutanoic acid and 3,3-difluoroazetidine hydrochloride (CAN 288315-03-7)) as starting materials. MS (EI): m/e=473.0 [M+H]+.

Sources & evidence

ORD record
ord-2c72c52836244c559ebe4c4584ad22ac
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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