Diisopropylethylamine → N-((2'-methyl-[2,4'-bipyridin]-5-yl)methyl)-6-phenoxynicotinamide

HRID 711285Notes

Reaction equation

HRID 711285 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][NH2:15])=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.[O:16]([C:23]1[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][N:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:27](=[O:28])[C:26]3[CH:30]=[CH:31][C:23]([O:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[N:24][CH:25]=3)=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27764976-Phenoxynicotinic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67208679(2'-Methyl-[2,4'-bipyridin]-5-yl)methanamine

Product 1

HCID 66632184N-((2'-methyl-[2,4'-bipyridin]-5-yl)methyl)-6-phenoxynicotinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (2′-methyl-[2,4′-bipyridin]-5-yl)methanamine 18-2 (20 mg, 0.10 mmol), 6-phenoxynicotinic acid 56-1 (21.5 mg, 0.10 mmol), and HATU (40 mg, 0.105 mmol) were added N,N-diisopropylethylamine (DIEA, 26 μL, 0.15 mmol) and DMF (0.5 mL). The solution was stirred overnight at room temperature and was subjected to reverse phase preparative HPLC separation to yield N-((2′-methyl-[2,4′-bipyridin]-5-yl)methyl)-6-phenoxynicotinamide 94 as a solid. MS m/z 397.2 (M+1).

Workup

  1. customphase preparative HPLC separation

Sources & evidence

ORD record
ord-29163bc76b2f4a80a071d1799faaa14d
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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