Phenyl isocyanate → 1-[4-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)cyclopent-2-enyl]3-phenyl-urea

HRID 1838451Notes

Reaction equation

HRID 1838451 reaction equation
[NH2:1][CH:2]1[CH2:6][CH:5]([N:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([Cl:17])[C:11]=3[C:10]3=[N:18][O:19][C:20]([CH3:21])=[C:9]3[C:8]2=[O:22])[CH:4]=[CH:3]1.[N:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[C:24]=[O:25]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:17][C:12]1[C:11]2[C:10]3[C:9](=[C:20]([CH3:21])[O:19][N:18]=3)[C:8](=[O:22])[N:7]([CH:5]3[CH2:6][CH:2]([NH:1][C:24]([NH:23][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:25])[CH:3]=[CH:4]3)[C:16]=2[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 120949645-(4-amino-cyclopent-2-enyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one

Product 1

HCID 187536981-[4-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)cyclopent-2-enyl]3-phenyl-ureaYield 50.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 5-(4amino-cyclopent-2-enyl)9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one (50 mg, 0.16 mmol) in CH2Cl2 (2 mL) was added isocyanatobenzene (0.018 mL, 0.18 mmol) and DMAP (catalytic amount) and stirred at r.t for 2 hours. The mixture was diluted with CH2Cl2, washed (brine), dried (Na2SO4), filtered and concentrated Column chromatography (silica gel, hexanes/ethyl acetate, gradient) gave the tide compound (35 mg, 50%). Mass Spectrum (M) (m/z) 433.3 (M−1). Anal. Calc. For C23H19ClN4O3; Theoretical: C, 63.52, H, 4.40, N, 12.88%; Found: C, 63.82, H, 4.45, N, 12.49%.

Workup

  1. washwashed (brine)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated Column chromatography (silica gel, hexanes/ethyl acetate, gradient)

Sources & evidence

ORD record
ord-5a1bbc95cfc14600b9ee1ca5a33c3d4c
Source dataset
uspto-grants-2004_01
Patent number
US06673809B2

Reaction notes

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