5-Bromo-2-(trifluoromethyl)pyridine → HCID 68818024, compound

HRID 734355Notes

Reaction equation

HRID 734355 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1.[ClH:12].Cl.[CH:14]1([N:18]2[CH2:23][CH2:22][N:21]([C:24]([CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[O:25])[CH2:20][CH2:19]2)[CH2:17][CH2:16][CH2:15]1>>[ClH:12].[CH:14]1([N:18]2[CH2:23][CH2:22][N:21]([C:24]([CH:26]3[CH2:31][CH2:30][N:29]([C:2]4[CH:7]=[N:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=4)[CH2:28][CH2:27]3)=[O:25])[CH2:20][CH2:19]2)[CH2:17][CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 27611975-Bromo-2-(trifluoromethyl)pyridineHCID 68816921Methanone, (4-cyclobutyl-1-piperazinyl)-4-piperidinyl-, hydrochloride (1:2)

Product 1

HCID 68818024HCID 68818024, compound

Procedure

The title compound (E97) was prepared in a similar manner to that described in Example 96, using 5-bromo-2-trifluoromethylpyridine (F. Cottet and M. Schlosser, Eur. J. Org. Chem., 2002, 327-330) and 1-cyclobutyl-4(piperidine-4-carbonyl)-piperazine (free base compound from D7). 1H NMR δ [DMSO-d6]: 1.53-1.83 (6H, m), 2.15 (2H, m), 2.39 (2H, br. m), 2.70 (1H, m), 2.84 (1H, m), 2.96 (3H, m), 3.07 (IH, m), 3.32 (2H, br. m), 3.52-3.68 (2H, m), ca 4.0 (2H, br., partially obscured by H2O signal), 4.22 (1H, br. d, J≈14 Hz), 4.46 (1H, br., J≈14 Hz), 7.44 (IH, dd, J=9, 3 Hz), 7.62 (1H, d, J=9 Hz), 8.43 (1H, d, J=3 Hz), 11.54 (1H, br.); LCMS electrospray (+ve) 411 (MH+).

Sources & evidence

ORD record
ord-e62c1865d88e4edda3dce2daa21c9861
Source dataset
uspto-grants-2009_09
Patent number
US07592347B2

Reaction notes

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