1-(Piperidin-4-yl)-1,3-diazinan-2-one → 3-[1-(3,4-Dichlorophenyl)-3-(4-(2-oxoperhydropyrimidine-1-yl)piperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochloride

HRID 725073Notes

Reaction equation

HRID 725073 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[N:14]2[CH3:23])[CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[O:24]=[C:25]1[NH:30][CH2:29][CH2:28][CH2:27][N:26]1[CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[N:14]2[CH3:23])[CH2:10][CH2:11][N:34]2[CH2:35][CH2:36][CH:31]([N:26]3[CH2:27][CH2:28][CH2:29][NH:30][C:25]3=[O:24])[CH2:32][CH2:33]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 155726661-(Piperidin-4-yl)-1,3-diazinan-2-oneHCID 218397793-(3,4-dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde

Product 1

HCID 218399643-[1-(3,4-Dichlorophenyl)-3-(4-(2-oxoperhydropyrimidine-1-yl)piperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochlorideYield 160.7%

Procedure

3-(3,4-Dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.333 g) was coupled to 4-(2-oxoperhydropyrimidine-1-yl)piperidine (0.183 g) by a method similar to that described in Example 8. The reaction product was purified by chromatography and converted to the corresponding hydrochloride salt as described in Example 8 to afford the title compound (0.424 g); mp 160°-185° C.; MS: m/z=514(M+1); NMR(CD3SOCD3): 1.65 (d,2, J=13), 1.78 (s,1), 2.18 (m,2), 3.06 (s,3) 4.39 (m,1), 4.87 (d,1, J=3.5), 6.77 (d,1, J=8.4), 6.96 (s,1), 7.33 (d,1, J=8.3), 7.50 (m,2), 7.67 (m,1), 7.94 (d,1, J=7.6). Analysis for C27H32 Cl2N4O2.2.0 HCl.0.5 H2O: Calculated: C, 54.28; H, 5.90, N, 9.37; Found: C, 54.36; H, 5.86; N, 9.10.

Workup

  1. customThe reaction product was purified by chromatography

Sources & evidence

ORD record
ord-c511b1ef98a04354a6b6df094ec22685
Source dataset
uspto-grants-1998_01
Patent number
US05705505

Reaction notes

Loading…