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

HRID 632369Notes

Reaction equation

HRID 632369 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([NH:14][C:15]([CH2:21][CH3:22])([CH2:19][CH3:20])[C:16]([OH:18])=O)=[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.[F:29][C:30]1([F:34])[CH2:33][NH:32][CH2:31]1>>[F:29][C:30]1([F:34])[CH2:33][N:32]([C:16]([C:15]([NH:14][C:12]([C:10]2[CH:9]=[CH:8][C:7]([N:23]3[CH2:24][C:25]([F:28])([F:27])[CH2:26]3)=[C:6]([O:5][CH2:4][CH:1]3[CH2:2][CH2:3]3)[N:11]=2)=[O:13])([CH2:21][CH3:22])[CH2:19][CH3:20])=[O:18])[CH2:31]1

Participants

3

Reactant 2

HCID 27582483,3-DifluoroazetidineHCID 710877392-(6-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinamido)-2-ethylbutanoic acid

Product 1

HCID 710935796-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid [1-(3,3-difluoro-azetidine-1-carbonyl)-1-ethyl-propyl]-amide

Procedure

In analogy to the procedure described in Example 293, 2-(6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinamido)-2-ethylbutanoic acid and 3,3-difluoroazetidine (CAN 679431-52-8) were condensed to the title product. MS (EI): m/e=471.4 [M−H]−.

Sources & evidence

ORD record
ord-70fc0644e7e240518b5d7e71d34ee09f
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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