3,3-Difluoroazetidine hydrochloride → 5-(3,3-Difluoroazetidin-1-yl)-N-((S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-6-((tetrahydrofuran-2-yl)methoxy)picolinamide

HRID 927652Notes

Reaction equation

HRID 927652 reaction equation
Cl.[F:2][C:3]1([F:7])[CH2:6][NH:5][CH2:4]1.[CH3:8][C:9]([CH3:33])([CH3:32])[C@H:10]([NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21](Br)=[C:20]([O:25][CH2:26][CH:27]2[CH2:31][CH2:30][CH2:29][O:28]2)[N:19]=1)=[O:17])[C:11](=[O:14])[NH:12][CH3:13]>>[F:2][C:3]1([F:7])[CH2:6][N:5]([C:21]2[CH:22]=[CH:23][C:18]([C:16]([NH:15][C@@H:10]([C:9]([CH3:33])([CH3:32])[CH3:8])[C:11]([NH:12][CH3:13])=[O:14])=[O:17])=[N:19][C:20]=2[O:25][CH2:26][CH:27]2[CH2:31][CH2:30][CH2:29][O:28]2)[CH2:4]1

Participants

3

Reactant 2

HCID 27582473,3-Difluoroazetidine hydrochlorideHCID 711056445-Bromo-6-(tetrahydro-furan-2-ylmethoxy)-pyridine-2-carboxylic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-amide

Product 1

HCID 710880055-(3,3-Difluoroazetidin-1-yl)-N-((S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-6-((tetrahydrofuran-2-yl)methoxy)picolinamide

Procedure

The title compound was synthesized by addition of 3,3-difluoroazetidine hydrochloride (CAN 288315-03-7) to 5-bromo-6-(tetrahydro-furan-2-ylmethoxy)-pyridine-2-carboxylic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-amide (Example 188) in analogy to the procedure described in Example 69 a, MS (EI): m/e=441.0 [M+H]+.

Sources & evidence

ORD record
ord-1abb010a623c4e94807ae96365b25aed
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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