HCID 86666964, compound → 6-[(6-Chloropyridin-3-yl)methyl]-3-piperidin-4-ylbenzo[h]quinazolin-4(3H)-one

HRID 82474Notes

Reaction equation

HRID 82474 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11]3[C:16](=[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=24)[N:15]=[CH:14][N:13]([CH:23]2[CH2:28][CH2:27][N:26](C(OCC4C=CC=CC=4)=O)[CH2:25][CH2:24]2)[C:12]3=[O:39])=[CH:4][CH:3]=1>Br.C(O)(=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11]3[C:16](=[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=24)[N:15]=[CH:14][N:13]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[C:12]3=[O:39])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86666964HCID 86666964, compound

Product 1

HCID 510010206-[(6-Chloropyridin-3-yl)methyl]-3-piperidin-4-ylbenzo[h]quinazolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

A solution of benzyl 4-[6-[(6-chloropyridin-3-yl)methyl]-4-oxobenzo[h]quinazolin-3 (4H)-yl]piperidine-1-carboxylate (0.130 g, 0.241 mmol) in 3 mL of HBr/acetic acid solution (48.0% wt, 264 mmol) was stirred at rt for 3 h. The mixture was concentrated in vacuo and azetroped 3× with toluene. The residue was purified via preparative reverse phase HPLC to provide the title compound that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 404.9 for M+H+: 1H NMR (400 MHz, d6-DMSO) δ 9.07 (d, J=7.7 Hz, 1H), 8.47 (s, 1H), 8.30 (s, 1H), 8.12 (d, J=7.9 Hz, 1H), 8.11 (s, 1H), 7.80-7.66 (m, 3H), 7.37 (d, J=8.3 Hz, 1), 3.64 (s, 2H), 3.65-3.61 (m, 2H), 3.31-3.23 (m, 2H), 2.62-2.52 (m, 2H), 2.26 (d, J=12.5 Hz, 2H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified via preparative reverse phase HPLC

Sources & evidence

ORD record
ord-99c940933d87410b94ffc64dc46fbfa3
Source dataset
uspto-grants-2014_09
Patent number
US08846702B2

Reaction notes

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