HCID 11508324, compound → HCID 11580375, compound

HRID 1668780Notes

Reaction equation

HRID 1668780 reaction equation
[CH3:1][C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([N:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:23]([O-])=O)[CH:8]=2)[N:3]=1>C(OCC)(=O)C.CO.[Pd]>[NH2:23][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([CH3:1])[N:11]=[C:10]2[N:12]([C:14]1[CH:19]=[CH:18][C:17]([N:20]([CH3:21])[CH3:22])=[CH:16][CH:15]=1)[CH3:13]

Participants

5

Reactant 1

HCID 11508324HCID 11508324, compound

Product 1

HCID 11580375HCID 11580375, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2-methyl-6-nitroquinazolin-4-yl)-(4-dimethylaminophenyl)-methylamine (214 mg, 0.634 mmol) in 20 mL of ethyl acetate and methanol (1:1) with 5% Palladium on carbon was hydrogenated at 70 psi for 5 h. The reaction mixture was filtered and concentrated. The crude product was purified by chromatography (5% methanol/methylene chloride) to give the title compound (195 mg, 0.634 mmol, 100%). 1H NMR (CDCl3): 7.58 (d, J=8.7, 1H), 7.02 (m, 2H), 6.97 (dd, J=9.0, 2.7, 1H), 6.69 (m, 2H), 6.21 (d, J=2.4, 1H), 3.54 (s, 3H), 3.45 (s, broad, 2H), 2.97 (s, 6H), 2.67 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe crude product was purified by chromatography (5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-0c5957d083b9403ea689e9b2378f26ab
Source dataset
uspto-grants-2011_08
Patent number
US07989462B2

Reaction notes

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