1-(Piperidin-4-yl)-1,3-diazinan-2-one → HCID 21839891, compound

HRID 1738971Notes

Reaction equation

HRID 1738971 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]([C:22]([NH2:24])=[O:23])=[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]([C:22]([NH2:24])=[O:23])=[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 21839947HCID 21839947, compound

Product 1

HCID 21839891HCID 21839891, compoundYield 124.9%

Procedure

3-(3,4-Dichlorophenyl)-3-(5-aminocarbonyl-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionaldehyde (0.2 g) was coupled to 4-(2-oxoperhydropyrimidine-1-yl)piperidine (0.093 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 (0.19 g); mp 240-250° C. (d); MS: m/z=558(M+1); NMR: 2.60-2.77 (m,3), 3.29 (broad,3), 4.67 (m,1), 5.21 (s,1), 6.63 (m,1), 6.85 (s,1), 7.19 (d, J=8, 1), 7.63-7.82 (m,3). Analysis for C27H31Cl2N4O2Br.1.0H2O.1.3HCl.0.2C4H10O: Calculated: 54.16; H, 6.04, N, 10.96; Found: C, 54.21; H, 5.86; N, 10.74.

Workup

  1. customThe reaction product was not purified by chromatography

Sources & evidence

ORD record
ord-0c4c1570577448dab11c90667dfd1cce
Source dataset
uspto-grants-1999_10
Patent number
US05965576

Reaction notes

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