6-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acid → HCID 76281599, compound

HRID 625008Notes

Reaction equation

HRID 625008 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]([F:32])([F:31])[CH:24]([CH:26]1[CH2:30][CH2:29][NH:28][CH2:27]1)[OH:25]>>[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([N:28]3[CH2:29][CH2:30][CH:26]([CH:24]([OH:25])[C:23]([F:31])([F:32])[F:22])[CH2:27]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 902044161613292-86-6

Product 1

HCID 76281599HCID 76281599, compoundYield 46%

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 2,2,2-trifluoro-1-(pyrrolidin-3-yl)ethanol hydrochloride (CAN of corresponding free base: 943906-23-8, 14.5 mg, 70.4 μmol) to obtain the title compound (14 mg, 46%) as colorless liquid, MS (EI): m/e=436.4 [MH+].

Sources & evidence

ORD record
ord-c849ed94491a4b9bb197021689e64270
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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