6-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acid → HCID 90203742, compound

HRID 625027Notes

Reaction equation

HRID 625027 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.[CH2:22]1[C:24]2([CH2:28][CH2:27][NH:26][CH:25]2[C:29]([NH2:31])=[O:30])[CH2:23]1.Cl.C1C2(CC(C(N)=O)NC2)C1>>[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([N:26]3[CH2:27][CH2:28][C:24]4([CH2:22][CH2:23]4)[CH:25]3[C:29]([NH2:31])=[O:30])=[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

4

Reactant 3

HCID 710872926-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acidHCID 90203077HCID 90203077, compoundHCID 90203616HCID 90203616, compound

Product 1

HCID 90203742HCID 90203742, compound

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, 80 mg, 281 μmol) was reacted with a mixture of 5-azaspiro[2.4]heptane-4-carboxamide hydrochloride and 5-azaspiro[2.4]heptane-6-carboxamide hydrochloride (Example 151 d, 59.7 mg, 338 μmol) to obtain the title compound after preparative chiral HPLC (22 mg, 19%) as off-white solid, MS (ESI): m/e=407.3 [MH+].

Sources & evidence

ORD record
ord-5969d5bb99ce42cd8a73d29b864a58b1
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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