Diisopropylethylamine → HCID 178458609, compound

HRID 1092245Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.CCN(C(C)C)C(C)C.[CH:21]([O:24][C:25]1[NH:29][N:28]=[C:27]([NH2:30])[CH:26]=1)([CH3:23])[CH3:22]>C1COCC1>[Cl:11][C:4]1[N:3]=[C:2]([NH:30][C:27]2[CH:26]=[C:25]([O:24][CH:21]([CH3:23])[CH3:22])[NH:29][N:28]=2)[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2,6-dichloro-3-nitropyridine (1.0 g, 5.3 mmol) and DIEA (0.77 ml, 4.4 mmol) in THF (20 ml) was added 5-isopropoxy-1H-pyrazol-3-amine (0.50 g, 3.5 mmol). The reaction mixture was stirred at 25° C. for 3 days and 60° C. for 1 hour. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane-EtOAc=3:1) to give the title compound as a yellow solid (0.62 g, 59%). 1H NMR (400 MHz) 12.25 and 11.66 (s, 1H), 10.46 and 10.13 (s, 1H), 8.56 (m, 1H), 7.11 and 7.02 (d, J=8.4 Hz, 1H), 6.08 and 5.97 (s, 1H), 4.70 and 4.48 (m, 1H), 1.32 and 1.27 (d, J=6.0 Hz, 6H). MS: Calcd.: 297; Found: [M+H]+ 298.

Workup

customThe solvent was removed under reduced pressure
customthe resulted residue was purified by column chromatography (hexane-EtOAc=3:1)

Sources & evidence

ORD record: ord-b01877dd19494b00870a483de2707532
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129403B2

Reaction notes

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