1,3-Cyclopentanedione → HCID 9967386, compound

HRID 1837064Notes

Reaction equation

HRID 1837064 reaction equation
[N+:1]([C:4]1[S:5][CH:6]=[C:7]([CH:9]=O)[CH:8]=1)([O-:3])=[O:2].[CH2:11]1[C:16](=O)[CH2:15][C:13](=[O:14])[CH2:12]1.[NH2:18][C:19]1[N:23]([CH3:24])[NH:22][C:21](=[O:25])[CH:20]=1>>[CH3:24][N:23]1[C:19]2[NH:18][C:16]3[CH2:11][CH2:12][C:13](=[O:14])[C:15]=3[CH:9]([C:7]3[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[S:5][CH:6]=3)[C:20]=2[C:21](=[O:25])[NH:22]1

Participants

4

Reactant 3

HCID 774661,3-CyclopentanedioneHCID 1447302-Nitrothiophene-4-carboxaldehydeHCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-one

Product 1

HCID 9967386HCID 9967386, compoundYield 72.2%

Procedure

2-Nitrothiophene-4-carboxaldehyde (0.16 g, 1.0 mmol), 1,3-cyclopentadione (0.1 g, 1.0 mmol), and 5-amino-1-methyl-1,2-dihydropyrazol-3-one (0.11 g, 1.0 mmol) were processed as described in Example 1 to provide 0.24 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.35 (m, 2H), 2.68 (m, 2H), 3.5 (s, 3H), 4.8 (s, 1H), 7.51 (d, 1H), 7.89 (d, 1H), 9.75 (bs, 1H), 10.47 (s, 1H); MS (ESI−) m/z 331 (M−H)−; Anal. calcd for C14H12N4O4S: C, 50.60; H, 3.64; N, 16.86. Found: C, 51.06; H, 3.68; N, 16.97.

Sources & evidence

ORD record
ord-e6b1395b32da4e7ba11781a7a3edcfc0
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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