Diisopropylethylamine → N-(3-fluoro-4-(2-methylpyridin-4-yl)benzyl)-4-(pyrimidin-5-yl)benzamide

HRID 711226Notes

Reaction equation

HRID 711226 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:15][NH2:16])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH3:14])[CH:9]=1.[N:17]1[CH:22]=[C:21]([C:23]2[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=2)[CH:20]=[N: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>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH3:14])[CH:9]=1)[CH2:15][NH:16][C:27](=[O:28])[C:26]1[CH:25]=[CH:24][C:23]([C:21]2[CH:20]=[N:19][CH:18]=[N:17][CH:22]=2)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 41872474-(Pyrimidin-5-yl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67208674(3-Fluoro-4-(2-methylpyridin-4-yl)phenyl)methanamine

Product 1

HCID 56595064N-(3-fluoro-4-(2-methylpyridin-4-yl)benzyl)-4-(pyrimidin-5-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (3-fluoro-4-(2-methylpyridin-4-yl)phenyl)methanamine 15-3 (10.8 mg, 0.05 mmol), 4-(pyrimidin-5-yl)benzoic acid 15-4 (10.0 mg, 0.05 mmol), and HATU (23 mg, 0.06 mmol) were added N,N-diisopropylethylamine (DIEA, 17 μL, 0.1 mmol) and DMF (0.5 mL). The solution was stirred overnight at room temperature and was subjected directly to reverse phase preparative HPLC to yield N-(3-fluoro-4-(2-methylpyridin-4-yl)benzyl)-4-(pyrimidin-5-yl)benzamide 15 as a white powder. MS m/z 399.2 (M+1).

Sources & evidence

ORD record
ord-bc7675e069a74e2dabd737374456f1ee
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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