5-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-one → 4-(4-bromo-3-chlorophenyl)-1-methyl-1,2,4,9-tetrahydropyrano[3,4-b]pyrazolo[4,3-e]pyridine-3,5(6H,8H)-dione

HRID 1862433Notes

Reaction equation

HRID 1862433 reaction equation
[O:1]1[CH2:6][C:5](=O)[CH2:4][C:3](=[O:8])[CH2:2]1.[Cl:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[Br:18])[CH:13]=O.[NH2:19][C:20]1[N:24]([CH3:25])[NH:23][C:22](=[O:26])[CH:21]=1>>[Br:18][C:17]1[CH:16]=[CH:15][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:11][C:10]=1[Cl:9]

Participants

4

Reactant 3

HCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-oneHCID 3252872H-pyran-3,5(4H,6H)-dioneHCID 140498064-Bromo-3-chlorobenzaldehyde

Product 1

HCID 102730104-(4-bromo-3-chlorophenyl)-1-methyl-1,2,4,9-tetrahydropyrano[3,4-b]pyrazolo[4,3-e]pyridine-3,5(6H,8H)-dioneYield 70.7%

Procedure

2H-Pyran-3,5(4H,6H)-dione (0.057 g, 05 mmol), 3-chloro4-bromo-benzaldehyde (0.11 g, 0.5 mmol), and 5-amino-1-methyl-1,2-dihydropyrazol-3-one (0.056g, 0.5 mmol) were processed as described in Example 26C to provide 0.145 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 3.5 (s, 3H), 4.0 (s, 2H), 4.52 (q, 2H), 4.92 (s, 1H), 7.03 (dt, 1H), 7.32(t, 1H), 7.6 (dd, 1H), 9.62 (s, 1H), 10.1 (s, 1H); MS (ESI−) m/z 410 (M−H:) Anal. calcd for C16H13N3BrClO3: C, 46.80;H,3.19; N, 10.23. Found: C, 46.77;H, 3.43; N, 10.27.

Sources & evidence

ORD record
ord-d80d745392fc4a5d8731cd3497ecb475
Source dataset
uspto-grants-2003_03
Patent number
US06538004B2

Reaction notes

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