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

HRID 725112Notes

Reaction equation

HRID 725112 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[CH2:23][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](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[N:14]2[CH2:23][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 218397513-(3,4-dichlorophenyl)-3-(2-ethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde

Product 1

HCID 218399733-[1-(3,4-Dichlorophenyl)-3-(4-(2-oxoperhydropyrimidin-1-yl)piperidino)propyl]-2-ethyl-2,3-dihydroisoindol-1-one hydrochlorideYield 81.8%

Procedure

A solution of 3-(3,4-dichlorophenyl)-3-(2-ethyl-3-oxo-2,3-dihydroisoindol-1-yl)propionaldehyde (0.36 g) was treated with 4-(2-oxoperhydropyrimidin-1-yl)piperidine (0.183 g) as described in Example 8. The resulting material was purified by chromatography and was transformed into the hydrochloride to afford the title compound (0.23 g); mp 165°-170° C.; MS: m/z=557(M+1); NMR(CD3OD): 2.3 (m,7), 2.9 (m,10), 3.45 (m,1), 4.0 (m,1), 4.3 (m,1), 5.0 (m,1), 7.25 (m,7). Analysis for C28H34Cl2N4 O2.1.0 HCl.1.2 H2O: Calculated: C, 57.23; H, 6.41; N, 9.53; Found: C, 57.16; H, 6.21; N, 9.28.

Workup

  1. customThe resulting material was purified by chromatography

Sources & evidence

ORD record
ord-9f259a12ea74457bae2646765f086de5
Source dataset
uspto-grants-1998_01
Patent number
US05705505

Reaction notes

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