5-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-one → HCID 10274750, compound

HRID 1862432Notes

Reaction equation

HRID 1862432 reaction equation
[O:1]1[CH2:6][C:5](=O)[CH2:4][C:3](=[O:8])[CH2:2]1.[I:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[CH3:18])[CH:13]=O.[NH2:19][C:20]1[N:24]([CH3:25])[NH:23][C:22](=[O:26])[CH:21]=1>>[I:9][C:10]1[CH:11]=[C:12]([CH:13]2[C:21]3[C:22](=[O:26])[NH:23][N:24]([CH3:25])[C:20]=3[NH:19][C:5]3[CH2:6][O:1][CH2:2][C:3](=[O:8])[C:4]2=3)[CH:15]=[CH:16][C:17]=1[CH3:18]

Participants

4

Reactant 3

HCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-oneHCID 3252872H-pyran-3,5(4H,6H)-dioneHCID 123302543-Iodo-4-methylbenzaldehyde

Product 1

HCID 10274750HCID 10274750, compoundYield 42.7%

Procedure

2H-Pyran-3,5(4H,6H)-dione (0.085 g, 0.75 mmol), 3-iodo4-methyl-benzaldehyde (0.18 g, 0.75 mmol), and 5-amino-1-methyl-1,2-dihydropyrazol-3-one (0.084 g, 0.75 mmol) were processed as described in Example 26C to provide 0.14 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 2.38 (s, 3H), 3.49 (s, 3H), 4.0 (s, 2H), 4.52 (q, 2H), 4.88 (s, 1H), 7.05 (dd, 1H), 7.16(d, 1H), 7.56 (d, 1H), 9.58 (bs, 1H), 10.03 (s, 1H); MS (ESI−) m/z 436 (M−H)−; Anal. calcd for C17H16N3IO3.0.5 C2H5OH: C, 46.97;H, 4.16; N, 9.13. Found: C, 46.60;H, 4.42; N, 9.32.

Sources & evidence

ORD record
ord-84837318849c4775a49c986a78397f20
Source dataset
uspto-grants-2003_03
Patent number
US06538004B2

Reaction notes

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