2,6-Diisopropylphenyl isocyanate → N-[2,6-bis(1-methylethyl)phenyl]-N'-[3-[(dibutylamino)methyl]-1-(phenylmethyl)-1H-pyrazol-5-yl]urea

HRID 373178Notes

Reaction equation

[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([CH2:14][N:15]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])[CH:3]=1.[CH:24]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH:33]([CH3:35])[CH3:34])[C:28]=1[N:36]=[C:37]=[O:38])([CH3:26])[CH3:25]>C(#N)C>[CH3:26][CH:24]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH:33]([CH3:34])[CH3:35])[C:28]=1[NH:36][C:37]([NH:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([CH2:14][N:15]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])[CH:3]=1)=[O:38])[CH3:25]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 5-amino-3-[(dibutylamino)methyl]-1-(phenylmethyl)-1H-pyrazole (0.70 g, 2.2 mmol), 2,6-diisopropylphenylisocyanate (0.48 mL, 2.2 mmol), and cuprous iodide (cat) in acetonitrile was heated to reflux for 16 hours. The resulting solution was cooled (25° C.), concentrated in vacuo, and chromatographed on silica (90:10 hexane:ethyl acetate). The product containing fractions were combined and concentrated in vacuo. The resulting oil was crystallized from hexane to yield 0.40 g (34.7%) of the title compound as a white powder, m.p. 149°-151.5° C.

Workup

temperatureto reflux for 16 hours
concentrationconcentrated in vacuo
customchromatographed on silica (90:10 hexane:ethyl acetate)
additionThe product containing fractions
concentrationconcentrated in vacuo
customThe resulting oil was crystallized from hexane

Sources & evidence

ORD record: ord-81214bacb100489380372f6b749f93ee
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05162360

Reaction notes

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