HCID 22649188, compound → HCID 22649208, compound

HRID 1782079Notes

Reaction equation

HRID 1782079 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]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-])=O)=[O:17]>[Pd].CN(C=O)C>[NH2:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[NH:18][C:16]([NH:15][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1)=[O:17]

Participants

4

Reactant 1

HCID 22649188HCID 22649188, compound

Product 1

HCID 22649208HCID 22649208, compoundYield 82.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(6,7dimethoxyquinazolin-4-yl)-3-(2-nitrophenyl)urea (0.18 g), 10% palladium charcoal catalyst (0.023 g) and DMF (10 ml) was stirred at ambient temperature under an atmosphere of hydrogen for 16 hours. The reaction mixture was filtered and the filtrate was evaporated. The resultant gum was triturated under ethyl acetate and there was thus obtained the title compound as a solid (0.137 g); NMR Spectrum: (DMSOd6) 3.95-3.95 (br s, 8H), 6.63 (t, 1H), 6.81 (d, 1H), 6.91 (t, 1H), 7.25 (s, 1H), 7.47 (d, 1H), 8.05 (s, 1H), 8.64 (s, 1H), 10.28 (br, s, 1H), 11.74 (br, s, 1H); Mass spectrum M+H+340.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe resultant gum was triturated under ethyl acetate

Sources & evidence

ORD record
ord-e167641bb4ba41f38ad99a7e66918a01
Source dataset
uspto-grants-2009_03
Patent number
US07498335B2

Reaction notes

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