1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 66875979, compound

HRID 871770Notes

Reaction equation

[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:19])OC2C=CC=CC=2)[N:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:26][C:27]1[CH:28]=[C:29]([OH:34])[CH:30]=[CH:31][C:32]=1[F:33].C1CCN2C(=NCCC2)CC1>C(#N)C>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:26][C:27]2[CH:28]=[C:29]([OH:34])[CH:30]=[CH:31][C:32]=2[F:33])=[O:19])[N:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:6]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred suspension of phenyl 3-tert-butyl-1-phenyl-1H-pyrazol-5-ylcarbamate (prepared as described in example 153A) (335 mg, 1 mmol) and 3-amino-4-fluorophenol (127 mg, 1 mmol) in acetonitrile (15 mL) at rt, was added DBU (0.3 mL, 2 mmol). The mixture was heated at 50° C. for 1 h. The reaction mixture was cooled to rt, concentrated under reduced pressure, and the residue purified via silica gel column chromatography to afford 1-(3-tert-butyl-1-phenyl-1H-pyrazol-5-yl)-3-(2-fluoro-5-hydroxyphenyl)urea (217 mg, 59%) as a solid. LC-MS (ESI) m/z 369 (M+H)+.

Workup

temperatureThe reaction mixture was cooled to rt
concentrationconcentrated under reduced pressure
customthe residue purified via silica gel column chromatography

Sources & evidence

ORD record: ord-8c9ae1c8952f4b7f8276178e210db625
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969587B2

Reaction notes

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