1-(Piperidin-4-yl)-1,3-diazinan-2-one → HCID 21839895, compound

HRID 725104Notes

Reaction equation

HRID 725104 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[C:17]([Cl:22])[CH:18]=[CH:19][CH:20]=3)[C:15](=[O:23])[N:14]2[CH3:24])[CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[O:25]=[C:26]1[NH:31][CH2:30][CH2:29][CH2:28][N:27]1[CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[C:17]([Cl:22])[CH:18]=[CH:19][CH:20]=3)[C:15](=[O:23])[N:14]2[CH3:24])[CH2:10][CH2:11][N:35]2[CH2:36][CH2:37][CH:32]([N:27]3[CH2:28][CH2:29][CH2:30][NH:31][C:26]3=[O:25])[CH2:33][CH2:34]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 155726661-(Piperidin-4-yl)-1,3-diazinan-2-oneHCID 21839990HCID 21839990, compound

Product 1

HCID 21839895HCID 21839895, compoundYield 41.3%

Procedure

3-(3,4-Dichlorophenyl)-3-(4-chloro-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.695 g) was coupled to 4-(2-oxoperhydropyrimidine-1-yl)piperidine (0.31 g) by a method similar to that described in Example 8. The reaction product was not purified by chromatography but converted to the hydrochloride salt to afford the title compound (0.220 g); mp 175°-185° C.; MS: m/z=549(M+1); NMR(CD3OD): 1.92 (m,4), 2.13 (m,2), 2.54 (m,2), 3.29 (s,3), 3.66 (m,3), 4.37 (m,1), 6.76 (dd,1, J=8.3, 21), 6.96 (d,1, J=21), 7.29 (d,1, J=8), 7.5 (d,1, J=8), 7.65 (t,1, J=7.8), 7.83 (d,1, J=7.5). Analysis for C29H31Cl3N4O2.2.5 H2O.1.0 HCl: Calculated: C, 53.14; H, 5.69, N, 8.55; Found: C, 53.13; H, 5.67; N, 9.51.

Workup

  1. customThe reaction product was not purified by chromatography

Sources & evidence

ORD record
ord-d3f710e9e2eb4b839cbd5369099d9998
Source dataset
uspto-grants-1998_01
Patent number
US05705505

Reaction notes

Loading…