6-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acid → HCID 118451454, compound

HRID 625012Notes

Reaction equation

HRID 625012 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.[OH:22][C:23]1([CH3:31])[CH2:27][NH:26][C@H:25]([C:28]([NH2:30])=[O:29])[CH2:24]1>>[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([N:26]3[CH2:27][C:23]([OH:22])([CH3:31])[CH2:24][C@H:25]3[C:28]([NH2:30])=[O:29])=[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 90203343HCID 90203343, compound

Product 1

HCID 118451454HCID 118451454, compoundYield 11.1%

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, 50 mg, 176 μmol) was reacted with (2S)-4-hydroxy-4-methylpyrrolidine-2-carboxamide hydrochloride (Example 132 b, 39.7 mg, 176 μmol) and purified by chiral HPLC to obtain the title compound (8 mg, 10%) as white solid, LC-MS (UV peak area, ESI) 93%, 411.1854 [MH+].

Workup

  1. custompurified by chiral HPLC

Sources & evidence

ORD record
ord-7d73743f782d41aba7d2523bb08e79cf
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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