Benzene, 1-isocyanato-2-methoxy- → CXCR2 antagonist 8

HRID 1385346

Reaction equation

HRID 1385346 reaction equation
[OH:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]=[C:21]=[O:22]>>[OH:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH:4][C:21]([NH:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[O:13][CH3:12])=[O:22]

Participants

3

Reactant 2

HCID 69695Benzene, 1-isocyanato-2-methoxy-HCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 9796445CXCR2 antagonist 8Yield 27%

Procedure

N-(2-Hydroxy-4-nitrophenyl)-N′-(2-methoxyphenyl)urea was prepared from 2-hydroxy 4-nitro aniline (154 mg, 1.0 mmol) and 2-methoxy phenyl isocyanate (1 mmol.) according to the procedure in General Method B. The product was purified by dilution with methylene chloride and precipitation with hexanes. Filtering afforded the title compound (82 mg, 27%). EI-MS m/z 302 (M−H)−

Workup

  1. customThe product was purified by dilution with methylene chloride and precipitation with hexanes
  2. filtrationFiltering

Sources & evidence

ORD record
ord-2ddabcb6303c49b89aff50ab6d7d7887
Source dataset
uspto-grants-2001_07
Patent number
US06262113B1

Linked notes

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