1-(Piperidin-4-yl)-1,3-diazinan-2-one → HCID 21839920, compound

HRID 725096Notes

Reaction equation

HRID 725096 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[CH:17][C:18]([O:22][CH2:23][CH3:24])=[CH:19][CH:20]=3)[C:15](=[O:25])[N:14]2[CH3:26])[CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[O:27]=[C:28]1[NH:33][CH2:32][CH2:31][CH2:30][N:29]1[CH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[CH:17][C:18]([O:22][CH2:23][CH3:24])=[CH:19][CH:20]=3)[C:15](=[O:25])[N:14]2[CH3:26])[CH2:10][CH2:11][N:37]2[CH2:38][CH2:39][CH:34]([N:29]3[CH2:30][CH2:31][CH2:32][NH:33][C:28]3=[O:27])[CH2:35][CH2:36]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 155726661-(Piperidin-4-yl)-1,3-diazinan-2-oneHCID 21839931HCID 21839931, compound

Product 1

HCID 21839920HCID 21839920, compoundYield 122.9%

Procedure

3-(3,4-Dichlorophenyl)-3-(5-ethoxy-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.3 g) was coupled to 4-(2-oxoperhydropyrimidine-1-yl)piperidine (0.135 g) by a method similar to that described in Example 8. The reaction product was not purified by chromatography but converted to the corresponding hydrochloride salt as described in the Example 8 to afford the title compound (0.28 g); mp 190°-200° C.; MS: m/z=559(M+1); NMR(CDCl3): 1.33 (t,6, J=6.9), 1.71 (m,4), 2.20 (m,2), 2.5 (m,2), 2.74 (broad,1), 3.52 (m,3), 4.04 (m,2), 4.31 (m,1), 4.76 (m,2), 7.05 (m,5), 7.81 (d,1, J=8.41). Analysis for C29H36Cl2N4O3.2.0 HCl.0.5 H2O: Calculated: C, 54.30; H, 6.13, N, 8.73; Found: C, 54.02; H, 6.00; N, 8.47.

Workup

  1. customThe reaction product was not purified by chromatography

Sources & evidence

ORD record
ord-403c35d776b54496b733a0a2512af2f5
Source dataset
uspto-grants-1998_01
Patent number
US05705505

Reaction notes

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