Diisopropylethylamine → N-((2'-fluoro-[2,4'-bipyridin]-5-yl)methyl)-4-(pyrazin-2-yl)benzamide

HRID 711235Notes

Reaction equation

HRID 711235 reaction equation
[F: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.[N:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=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>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:26](=[O:27])[C:25]3[CH:24]=[CH:23][C:22]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][N:16]=4)=[CH:30][CH:29]=3)=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 114583014-Pyrazin-2-ylbenzoic acidHCID 67208618(2'-Fluoro-2,4'-bipyridin-5-yl)methanamine

Product 1

HCID 56598365N-((2'-fluoro-[2,4'-bipyridin]-5-yl)methyl)-4-(pyrazin-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (2′-fluoro-[2,4′-bipyridin]-5-yl)methanamine 24-2 (15 mg, 0.074 mmol), 4-(pyrazin-2-yl)benzoic acid 18-3 (18 mg, 0.09 mmol), and HATU (36 mg, 0.095 mmol) were added N,N-diisopropylethylamine (DIEA, 26 μL, 0.15 mmol) and DMF (0.6 mL). The solution was stirred overnight at room temperature and was subjected directly to reverse phase preparative HPLC to yield N-((2′-fluoro-[2,4′-bipyridin]-5-yl)methyl)-4-(pyrazin-2-yl)benzamide 24 as a solid. MS m/z 386.2 (M+1).

Sources & evidence

ORD record
ord-cdae7e941e574b17b7dad478dccb3cd6
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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