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-thiazol-2-yl-ethyl)-amide

HRID 632192Notes

Reaction equation

HRID 632192 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.[CH:21]1([CH2:24][C@H:25]([NH:31]C(C2C=CC(C3CCOCC3)=C(OCC3CC3)N=2)=O)[C:26]2[S:27][CH:28]=[CH:29][N:30]=2)[CH2:23][CH2:22]1>>[CH:21]1([CH2:24][C@H:25]([NH:31][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:26]2[S:27][CH:28]=[CH:29][N:30]=2)[CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 710872926-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acidHCID 711055706-Cyclopropylmethoxy-5-(tetrahydro-pyran-4-yl)-pyridine-2-carboxylic acid ((S)-2-cyclopropyl-1-thiazol-2-yl-ethyl)-amide

Product 1

HCID 711056246-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid ((S)-2-cyclopropyl-1-thiazol-2-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 (S)-2-cyclopropyl-1-thiazol-2-yl-ethylamine (Example 59 b) as starting materials, MS (EI): m/e=435.1 [M+H]+.

Sources & evidence

ORD record
ord-25c971406d6044c58fd914c1e3678088
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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