4-Fluorophenyl isocyanate → HCID 21948172, compound

HRID 1839377Notes

Reaction equation

HRID 1839377 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[NH:11]([C:18]1[N:19]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:20]2[C:25]([C:26](=[O:28])[CH:27]=1)=[C:24]([CH3:29])[CH:23]=[C:22]([Cl:30])[N:21]=2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[Cl:30][C:22]1[N:21]=[C:20]2[C:25]([C:26](=[O:28])[CH:27]=[C:18]([N:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[O:10])[N:19]2[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[C:24]([CH3:29])[CH:23]=1

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanate2×HCID 21948152HCID 21948152, compound

Product 1

HCID 21948172HCID 21948172, compoundYield 1.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Fluorophenyl isocyanate (45.0 mg, 0.33 mmol) was added to a stirred solution of 2-anilino-7-chloro-5-methyl-1-phenyl-1,8-naphthyridin-4(1H)-one (100 mg, 0.276 mmol) in CH2Cl2 (3 mL). After 16 h, an additional equivalent of 4-fluorophenyl isocyanate (45.0 mg) was added, and the reaction stirred for an additional 16 h. The reaction was concentrated in vacuo and the residue was dissolved in EtOAc. The solution was washed with 1 N HCl, dried over MgSO4, and concentrated in vacuo. Purification of the residue using reverse phase prep-HPLC afforded N-(7-chloro-5-methyl-4-oxo-1-phenyl-1,4-dihydro-1,8-naphthyridin-2-yl)-N′-(4-fluorophenyl)-N-phenylurea (2.2 mg, 1.6%): LCMS RT: 3.47 min, MH+: 499.1, Rf=0.52 (1:1 EtOAc:Hex).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe solution was washed with 1 N HCl
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue

Sources & evidence

ORD record
ord-97f7f77140ba428eb50baedecf804812
Source dataset
uspto-grants-2004_01
Patent number
US06677352B1

Reaction notes

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