6-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acid → 6-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid [2-cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

HRID 632420Notes

Reaction equation

HRID 632420 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[CH:8][C:7]=2[N:15]2[CH2:18][C:17]([F:20])([F:19])[CH2:16]2)[CH2:3][CH2:2]1.Cl.[CH:22]1([CH2:25][C:26]([NH2:34])([CH3:33])[C:27]2[N:31]=[C:30]([CH3:32])[O:29][N:28]=2)[CH2:24][CH2:23]1>>[CH:22]1([CH2:25][C:26]([NH:34][C:12]([C:10]2[CH:9]=[CH:8][C:7]([N:15]3[CH2:18][C:17]([F:20])([F:19])[CH2:16]3)=[C:6]([O:5][CH2:4][CH:1]3[CH2:2][CH2:3]3)[N:11]=2)=[O:14])([CH3:33])[C:27]2[N:31]=[C:30]([CH3:32])[O:29][N:28]=2)[CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 710872926-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acidHCID 710877902-Cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine hydrochloride

Product 1

HCID 711057176-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid [2-cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

Procedure

The title compound was synthesized in analogy to Example 1, using 6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (Example 69 b) and 2-cyclopropyl-1-methyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine hydrochloride as starting materials. MS (D): m/e=448.5 [M+H]+.

Sources & evidence

ORD record
ord-3d4135a8016249f09c26f292dbfe6ce7
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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