Diisopropylethylamine → 6-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)-N-((3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)methyl)picolinamide

HRID 624914Notes

Reaction equation

HRID 624914 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])[C:24]1[N:28]=[C:27]([CH2:29][NH2:30])[O:26][N:25]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>>[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([NH:30][CH2:29][C:27]3[O:26][N:25]=[C:24]([C:23]([F:32])([F:31])[F:22])[N:28]=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

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66687518[3-(Trifluoromethyl)-1,2,4-oxadiazol-5-yl]methanamine hydrochlorideHCID 710872926-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acid

Product 1

HCID 902037476-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)-N-((3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)methyl)picolinamide

Procedure

In analogy to the procedure described in Example 47 b), 6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (Example 1 b) was reacted with C-(3-trifluoromethyl-[1,2,4]oxadiazol-5-yl)-methyl amine hydrochloride (CAS 944905-93-5) in the presence of TBTU and DIEA to give the title compound as white solid; MS (EI): m/e=434.5 [MH+].

Sources & evidence

ORD record
ord-5f3ddd22e2d4470280ee174bf08b6d6f
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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