3-Chloro-2,4-pentanedione → [4-(2-Ethylamino-4-methyl-thiazol-5-yl)-pyrimidin-2-yl]-(3-nitro-phenyl)-amine

HRID 132534Notes

Reaction equation

HRID 132534 reaction equation
[CH2:1]([NH:3][C:4]1[S:5][C:6]([C:10](=O)[CH3:11])=[C:7]([CH3:9])[N:8]=1)[CH3:2].Cl[CH:14](C(=O)C)C(=O)C.[N+]([O-])(O)=O.[N+:25]([C:28]1[CH:29]=[C:30]([NH:34][C:35]([NH2:37])=[NH:36])[CH:31]=[CH:32][CH:33]=1)([O-:27])=[O:26]>>[CH2:1]([NH:3][C:4]1[S:5][C:6]([C:10]2[CH:11]=[CH:14][N:37]=[C:35]([NH:34][C:30]3[CH:31]=[CH:32][CH:33]=[C:28]([N+:25]([O-:27])=[O:26])[CH:29]=3)[N:36]=2)=[C:7]([CH3:9])[N:8]=1)[CH3:2]

Participants

4

Reactant 3

HCID 743283-Chloro-2,4-pentanedioneHCID 179897541-[2-(Ethylamino)-4-methyl-1,3-thiazol-5-yl]ethan-1-oneHCID 1785125133-Nitrophenylguanidine Nitrate

Product 1

HCID 9924838[4-(2-Ethylamino-4-methyl-thiazol-5-yl)-pyrimidin-2-yl]-(3-nitro-phenyl)-amine

Procedure

3-Dimethylamino-1-(2-ethylamino-4-methyl-thiazol-5-yl)-propenone was prepared by reaction between 1-(2-ethylamino-4-methyl-thiazol-5-yl)-ethanone and 3-chloro-pentane-2,4-dione. It was then condensed with N-(3-nitro-phenyl)-guanidine nitrate in the usual manner to afford the title compound. Yellow solid; 1H-NMR (DMSO-d6) δ: 1.14 (m, 3H, CH3), 2.47 (s, 3H, CH3), 3.23 (m, 2H, CH2), 6.99 (d, 1H, J=5.0 Hz, pyrimidinyl-H), 7.55 (m, 1H, Ph-H), 7.77 (m, 1H, Ph-H), 8.02 (m, 1H, Ph-H), 8.39 (d, 1H, J=5.0 Hz, pyrimidinyl-H), 8.47 (s, 1H, Ph-H), 9.98 (br. s, 1H, NH).

Sources & evidence

ORD record
ord-62542a013b1f4aab9845968d17ee734d
Source dataset
uspto-grants-2008_06
Patent number
US07388015B2

Reaction notes

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