6-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acid → 6-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid ((S)-2-cyclopropyl-1-dimethylcarbamoyl-ethyl)-amide

HRID 927701Notes

Reaction equation

HRID 927701 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.[NH2:22][C@@H:23]([CH2:29][CH:30]1[CH2:32][CH2:31]1)[C:24]([N:26]([CH3:28])[CH3:27])=[O:25]>>[CH:30]1([CH2:29][C@H:23]([NH:22][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])[C:24](=[O:25])[N:26]([CH3:27])[CH3:28])[CH2:32][CH2:31]1

Participants

3

Reactant 2

HCID 710872926-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acidHCID 86674779(S)-2-Amino-3-cyclopropyl-N,N-dimethylpropanamide hydrochloride

Product 1

HCID 711056766-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid ((S)-2-cyclopropyl-1-dimethylcarbamoyl-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 (S)-2-amino-3-cyclopropyl-N,N-dimethylpropanamide hydrochloride (Example 222 b) as starting materials. MS (EI): m/e=423.0 [M+H]+.

Sources & evidence

ORD record
ord-ed9a23a415b5491bb76cf267b5e60d1b
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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