4-Ethyl-2,3-dioxopiperazinecarbonyl chloride → 4-[3-(2,3-Dioxo-4-ethylpiperazine-1-carbonylamino)propyl]-2-fluoro-1-triphenylmethylimidazole

HRID 2412484Notes

Reaction equation

HRID 2412484 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[N:6]=[C:7]([F:29])[N:8]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=1.Cl[C:31]([N:33]1[CH2:38][CH2:37][N:36]([CH2:39][CH3:40])[C:35](=[O:41])[C:34]1=[O:42])=[O:32]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[O:42]=[C:34]1[C:35](=[O:41])[N:36]([CH2:39][CH3:40])[CH2:37][CH2:38][N:33]1[C:31]([NH:1][CH2:2][CH2:3][CH2:4][C:5]1[N:6]=[C:7]([F:29])[N:8]([C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=1)=[O:32]

Participants

5

Reactant 2

HCID 1088134-Ethyl-2,3-dioxopiperazinecarbonyl chlorideHCID 204323144-(3-Aminopropyl)-2-fluoro-1-triphenylmethylimidazole

Product 1

HCID 204323764-[3-(2,3-Dioxo-4-ethylpiperazine-1-carbonylamino)propyl]-2-fluoro-1-triphenylmethylimidazole

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Crude 4-(3-aminopropyl)-2-fluoro-1-triphenylmethylimidazole was dissolved in CH2Cl2 and treated with 4-dimethylaminopyridine and a solution of 1-chlorocarbonyl-4-ethylpiperazine-2,3-dione in CH2Cl2. Work-up by chromatography gave 4-[3-(2,3-dioxo-4-ethylpiperazine-1-carbonylamino)propyl]-2-fluoro-1-triphenylmethylimidazole, having the following n.m.r. spectrum in CDCl3 : 1.25 (t, 3H); 1.85 (quintet, 2H); 2.25-3.7 (m, 6H); 4.05 (q, 2H); 6.25 (s, 1H); 7.05-7.5 (m, 15H).

Sources & evidence

ORD record
ord-1e671b23657547fda9e6b13a21b10116
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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