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

HRID 1956630Notes

Reaction equation

HRID 1956630 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-3721cc09112f4f3c933583dbcb3d24f3
Source dataset
uspto-grants-1998_07
Patent number
US05780483

Reaction notes

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