HCID 57810258, compound → HCID 57810092, compound

HRID 1924133Notes

Reaction equation

HRID 1924133 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[NH:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:17]=1[F:25]>CN(C=O)C.CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[NH:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=1[F:25]

Participants

5

Reactant 1

HCID 57810258HCID 57810258, compound

Product 1

HCID 57810092HCID 57810092, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

(6,7-Dimethoxy-quinazolin-4-yl)-(2-fluoro-4-nitro-phenyl)-amine (673 mg, 1.95 mmol) was dissolved in a combination of DMF (20 ml) and MeOH (20 ml), to which was added 10% Pd/C (227 mg). The mixture was shaken under an atmosphere of H2 on a Parr hydrogenator at 40 psi for 3 hrs. The reaction mixture was filtered through celite and the filtrate concentrated in vacuo. The resulting residue was triturated in EtOAc/Et2O. The resulting solids were filtered, washed with Et2O, and dried under vacuum to give N1-(6,7-dimethoxy-quinazolin-4-yl)-2-fluoro-benzene-1,4-diamine (398 mg, 65%) which was used in the next reaction without further purification. 1H-NMR (400 MHz, DMSO): 10.80 (br s, 1H), 10.30 (br s, 1H), 8.63 (s, 1H), 8.15 (s, 1H), 7.33 (s, 1H), 7.15 (m, 1H), 6.45 (m, 1H), 3.96 (s, 6H). LC/MS Calcd for [M+H]+ 315.1, found 315.4.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe resulting residue was triturated in EtOAc/Et2O
  4. filtrationThe resulting solids were filtered
  5. washwashed with Et2O
  6. customdried under vacuum

Sources & evidence

ORD record
ord-73e8953376e74e3b9672d3385799f2c6
Source dataset
uspto-grants-2012_05
Patent number
US08178532B2

Reaction notes

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