Diisopropylethylamine → 4-(Pyrazin-2-yl)-N-(4-(2-(trifluoromethyl)pyridin-4-yl)benzyl)benzamide

HRID 711237Notes

Reaction equation

HRID 711237 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][NH2:16])=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1.[N:19]1[CH:24]=[CH:23][N:22]=[CH:21][C:20]=1[C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=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>[N:19]1[CH:24]=[CH:23][N:22]=[CH:21][C:20]=1[C:25]1[CH:26]=[CH:27][C:28]([C:29]([NH:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([C:7]3[CH:6]=[CH:5][N:4]=[C:3]([C:2]([F:1])([F:17])[F:18])[CH:8]=3)=[CH:14][CH:13]=2)=[O:30])=[CH:32][CH:33]=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 68080154(4-(2-(Trifluoromethyl)pyridin-4-yl)phenyl)methanamine

Product 1

HCID 565980884-(Pyrazin-2-yl)-N-(4-(2-(trifluoromethyl)pyridin-4-yl)benzyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (4-(2-(trifluoromethyl)pyridin-4-yl)phenyl)methanamine 28-3 (16 mg, 0.063 mmol), 4-(pyrazin-2-yl)benzoic acid 18-3 (13 mg, 0.065 mmol), and HATU (26 mg, 0.068 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 4-(pyrazin-2-yl)-N-(4-(2-(trifluoromethyl)pyridin-4-yl)benzyl)benzamide 28 as a solid. MS m/z 435.0 (M+1).

Sources & evidence

ORD record
ord-0f6851ca38c847708f66c1209fe29e17
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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