6-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acid → HCID 76281871, compound

HRID 625024Notes

Reaction equation

HRID 625024 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.[F:22][C:23]1([CH3:27])[CH2:26][NH:25][CH2:24]1>>[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([N:25]3[CH2:26][C:23]([F:22])([CH3:27])[CH2:24]3)=[O:14])[CH:9]=[CH:8][C:7]=2[N:15]2[CH2:18][C:17]([F:20])([F:19])[CH2:16]2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 710872926-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acidHCID 717579053-Fluoro-3-Methylazetidine hydrochloride

Product 1

HCID 76281871HCID 76281871, compoundYield 24%

Procedure

In analogy to the procedure described in Example 127 e), 6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (Example 1 b, 20 mg, 70.4 μmol) was reacted with 3-fluoro-3-methylazetidine hydrochloride (CAN 1427379-42-7, 10.6 mg, 84.4 μmol) to obtain the title compound (6 mg, 24%) as off-white solid, MS (ESI): m/e=356.2 [MH+].

Sources & evidence

ORD record
ord-14a62a4ccfdb4dc6adce4374447f6e87
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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