1,3-Cyclohexanedione, 4,4-dimethyl- → HCID 10276735, compound

HRID 1837072Notes

Reaction equation

HRID 1837072 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[NH:5][C:4](=[O:8])[CH:3]=1.[I:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH:13]=O.[CH3:19][C:20]1([CH3:28])[CH2:25][CH2:24][C:23](=O)[CH2:22][C:21]1=[O:27]>>[F:18][C:17]1[CH:16]=[CH:15][C:12]([CH:13]2[C:22]3[C:21](=[O:27])[C:20]([CH3:28])([CH3:19])[CH2:25][CH2:24][C:23]=3[NH:1][C:2]3[N:6]([CH3:7])[NH:5][C:4](=[O:8])[C:3]2=3)=[CH:11][C:10]=1[I:9]

Participants

4

Reactant 3

HCID 1363601,3-Cyclohexanedione, 4,4-dimethyl-HCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-oneHCID 103080734-Fluoro-3-iodobenzaldehyde

Product 1

HCID 10276735HCID 10276735, compoundYield 66%

Procedure

5-Amino-1-methyl-1,2-dihydropyrazol-3-one (0.06 g, 0.5 mmol), 3-iodo-4-fluorobenzaldehyde (0.125 g, 0.5 mmol), and 4,4-dimethyl-1,3-cyclohexanedione (0.07 g, 0.5 mmol) were processed as described in Example 22 to provide 0.15 g (66%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 0.92 (s, 3H), 0.98 (s, 3H), 1.78 (t, 2H), 2.63 (m, 2H), 3.42 (s, 3H), 4.81 (s, 1H), 7.05 (t, 1H), 7.1 (m, 1H), 7.5 (dd, 1H), 9.5 (s, 1H), 9.61 (s, 1H); MS (ESI−) m/z 466 (M−H)−; Anal. calcd for C19H19N3FIO2: C, 48.82; H, 4.07; N, 9.00.

Sources & evidence

ORD record
ord-7d9d1303274747ec8583e4d072f23189
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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