Phenyl isocyanate → HCID 86713652, compound

HRID 1430503Notes

Reaction equation

HRID 1430503 reaction equation
[NH2:1][C:2]1[C:3]([F:27])=[CH:4][C:5]([Cl:26])=[C:6]([C:8]2[C:9](=[O:25])[N:10]([CH2:23][CH3:24])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH2:19][CH2:20][S:21][CH3:22])[CH:12]=3)[CH:7]=1.[C:28]1([N:34]=[C:35]=[O:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[Cl:26][C:5]1[C:6]([C:8]2[C:9](=[O:25])[N:10]([CH2:23][CH3:24])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH2:19][CH2:20][S:21][CH3:22])[CH:12]=3)=[CH:7][C:2]([NH:1][C:35]([NH:34][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:36])=[C:3]([F:27])[CH:4]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 86713653HCID 86713653, compound

Product 1

HCID 86713652HCID 86713652, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(5-amino-2-chloro-4-fluorophenyl)-1-ethyl-7-(2-(methylthio)ethylamino)-1,6-naphthyridin-2(1H)-one (400 mg, 0.99 mmol) in DCM (20 mL) was added phenyl isocyanate (200 mg, 1.68 mmol) and the mixture was stirred overnight. The reaction mixture was quenched with MeOH and concentrated under reduced pressure. The residue was washed with Et2O to give 1-(4-chloro-5-(1-ethyl-7-(2-(methylthio)ethylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-phenylurea (200 mg, 39% yield).

Workup

  1. customThe reaction mixture was quenched with MeOH
  2. concentrationconcentrated under reduced pressure
  3. washThe residue was washed with Et2O

Sources & evidence

ORD record
ord-526fc489a1c94956a353963b26a0b509
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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