Piperazin-1-ol → 2-{2-Ethoxy-5-[4-(2-hydroxy-ethyl)-piperazine-1-sulfonyl]-phenyl}-5,7-dimethyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one

HRID 641212Notes

Reaction equation

HRID 641212 reaction equation
[CH2:1]([O:3]C1C=CC(S(Cl)(=O)=O)=CC=1C1NC(=O)C2=C(C)N=C(C)N2N=1)[CH3:2].ON1CCNCC1.[CH2:33]([O:35][C:36]1[CH:41]=[CH:40][C:39]([S:42]([N:45]2[CH2:50][CH2:49][N:48](O)[CH2:47][CH:46]2CC)(=[O:44])=[O:43])=[CH:38][C:37]=1[C:54]1[NH:59][C:58](=[O:60])[C:57]2=[C:61]([CH3:65])[N:62]=[C:63]([CH3:64])[N:56]2[N:55]=1)[CH3:34]>>[CH2:33]([O:35][C:36]1[CH:41]=[CH:40][C:39]([S:42]([N:45]2[CH2:50][CH2:49][N:48]([CH2:2][CH2:1][OH:3])[CH2:47][CH2:46]2)(=[O:43])=[O:44])=[CH:38][C:37]=1[C:54]1[NH:59][C:58](=[O:60])[C:57]2=[C:61]([CH3:65])[N:62]=[C:63]([CH3:64])[N:56]2[N:55]=1)[CH3:34]

Participants

4

Reactant 3

HCID 12463393Piperazin-1-olHCID 1358567774-Ethoxy-3-(5,7-dimethyl-4-oxo-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-2-yl)-benzenesulphonyl chlorideHCID 1363763942-[2-ethoxy-5-(4-hydroxy-ethylpiperazine-1-sulphonyl)-phenyl]-5,7-dimethyl-3H-imidazo[5,1-f]-[1,2,4]triazin-4-one

Product 1

HCID 1354840252-{2-Ethoxy-5-[4-(2-hydroxy-ethyl)-piperazine-1-sulfonyl]-phenyl}-5,7-dimethyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one

Procedure

By the same method, starting with 100 mg (0.261 mmol) of 4-ethoxy-3-(5,7-dimethyl-4-oxo-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-2-yl)-benzenesulphonyl chloride and 100 mg (0.784 mmol) of 4-hydroxypiperazine, 45 mg (36.1% of theory) of 2-[2-ethoxy-5-(4-hydroxy-ethylpiperazine-1-sulphonyl)-phenyl]-5,7-dimethyl-3H-imidazo[5,1-f]-[1,2,4]triazin-4-one are obtained.

Workup

  1. customare obtained

Sources & evidence

ORD record
ord-2de9771de3d34a3ca85d7df11b047c43
Source dataset
uspto-grants-2010_04
Patent number
US07696206B2

Reaction notes

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