1-(Piperidin-4-yl)-1,3-diazinan-2-one → HCID 21839756, compound

HRID 725098Notes

Reaction equation

HRID 725098 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]([F:22])=[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](=[CH:17][C:18]([F:22])=[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 21839908HCID 21839908, compound

Product 1

HCID 21839756HCID 21839756, compoundYield 142.8%

Procedure

3-(3,4-Dichlorophenyl)-3-(5-fluoro-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.27 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 (0.3 g); mp 180°-205° C. (d); MS: m/z=533(M+1); NMR(CD3 SOCD3): 1.73 (m,4), 2.17 (broad,2), 2.5 (broad,2), 2.74 (broad,1), 3.49 (m,5),3.69 (m,1), 4.36 (m,1), 4.86 (d,1, J=3.3), 6.75 (d,1, J=8.2) 7.07 (s,1), 7.35 (m,3), 7.92 (m,1). Analysis for C27H31 Cl2N4O4F.2.0 HCl: Calculated: C, 53.48; H, 5.49, N, 9.24; Found: C, 53.15; H, 5.53; N, 9.04.

Workup

  1. customThe reaction product was not purified by chromatography

Sources & evidence

ORD record
ord-06911a4aa10b4f63ba805caaf4a01087
Source dataset
uspto-grants-1998_01
Patent number
US05705505

Reaction notes

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