6-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acid → HCID 90204473, compound

HRID 624917Notes

Reaction equation

HRID 624917 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.[CH3:21][NH:22][C:23]1[C:27]([CH3:28])=[CH:26][N:25]([CH3:29])[N:24]=1>>[CH3:29][N:25]1[CH:26]=[C:27]([CH3:28])[C:23]([N:22]([CH3:21])[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])=[N:24]1

Participants

3

Reactant 2

HCID 710872926-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acidHCID 90203559HCID 90203559, compound

Product 1

HCID 90204473HCID 90204473, compound

Procedure

The title compound was synthesized in analogy to Example 47b), using 6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acid (Example 1 b) and N,1,4-trimethyl-1H-pyrazol-3-amine (which can be prepared from 3-formylamino-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester CAN 114936-04-8 via reduction with lithium aluminum hydride in diethyl ether at ambient temperature) as starting materials and isolated as colorless oil. MS (EI): m/e=392.5 [MH+].

Workup

  1. customisolated as colorless oil

Sources & evidence

ORD record
ord-ed1a2ea72c994340b668da0e65d21840
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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