1-(Piperidin-4-yl)-1,3-diazinan-2-one → HCID 21839912, compound

HRID 725100Notes

Reaction equation

HRID 725100 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[C:17]([F:25])[C:18]([F:24])=[C:19]([F:23])[C:20]=3[F:22])[C:15](=[O:26])[N:14]2[CH3:27])[CH2:10][CH:11]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[O:28]=[C:29]1[NH:34][CH2:33][CH2:32][CH2:31][N:30]1[CH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:13]2[C:21]3[C:16](=[C:17]([F:25])[C:18]([F:24])=[C:19]([F:23])[C:20]=3[F:22])[C:15](=[O:26])[N:14]2[CH3:27])[CH2:10][CH2:11][N:38]2[CH2:39][CH2:40][CH:35]([N:30]3[CH2:31][CH2:32][CH2:33][NH:34][C:29]3=[O:28])[CH2:36][CH2:37]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 155726661-(Piperidin-4-yl)-1,3-diazinan-2-oneHCID 21839764HCID 21839764, compound

Product 1

HCID 21839912HCID 21839912, compoundYield 145.7%

Procedure

3-(3,4-Dichlorophenyl)-3-(4,5,6,7-tetrafluoro-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.43 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 not purified by chromatography but converted to the corresponding hydrochloride salt as described in the Example 8 to afford the desired 3-[1-(3,4-Dichlorophenyl)-3-(4-(2-oxoperhydropyrimidine-1-yl)piperidino)propyl]-2-methyl-2,3-dihydro-4,5,6,7-terafluoro-isoindol-1-one hydrochloride (0.465 g); mp 220° C. (d); MS: m/z=587(M+1); NMR: 1.18 (m,4), 2.67 (m,4), 3.36 (s,3), 4.58 (m,1), 4.90 (s,1), 6.87-7.37 (m,3). Analysis for C27H28Cl2N4O2F4.1.5.HCl.2H2O: Calculated: C, 47.82; H, 4.98, N, 8.26; Found: C, 48.15; H, 4.73; N, 7.99.

Workup

  1. customThe reaction product was not purified by chromatography

Sources & evidence

ORD record
ord-e9784c0f8ef6446b99432d3200a521a1
Source dataset
uspto-grants-1998_01
Patent number
US05705505

Reaction notes

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