HCID 59242049, compound → HCID 59242042, compound

HRID 1876202Notes

Reaction equation

HRID 1876202 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N:10]([CH3:25])[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([N+:21]([O-])=O)[CH:19]=2)[N:14]=[C:13]([CH3:24])[N:12]=1.[H][H]>CC(O)=O.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N:10]([CH3:25])[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([NH2:21])[CH:19]=2)[N:14]=[C:13]([CH3:24])[N:12]=1

Participants

5

Reactant 2

HCID 59242049HCID 59242049, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59242042HCID 59242042, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

10% Pd—C (10 mg, 0.0094 mmol) was added to a soln of (2-fluoro-4-methoxy-phenyl)-methyl-(2-methyl-6-nitro-quinazolin-4-yl)-amine (127 mg, 0.371 mmol) in AcOH (3 mL) and this was reacted under 1 atm of hydrogen. After 3 h, the rxn was filtered through a 0.45 μm filter then concentrated. Satd NaHCO3 (10 mL) was added and the product extracted into CHCl3 (2×2 mL). The soln was dried (MgSO4), filtered through a plug of silica with an EtOAc wash then concd to a yellow crystalline solid (104 mg; 90%). 1H NMR (CDCl3) δ 7.61 (d, J=8.8 Hz, 1H), 7.05-6.99 (m, 2H), 6.73 (dd, J=2.8, 12 Hz, 1H), 6.66 (ddd, J=1.2, 3.2, 8.8 Hz, 1H), 6.18 (d, J=2.4 Hz, 1H), 3.82 (s, 3H), 3.51 (s(br), 2H), 3.50 (s, 3H), 2.69 (s, 3H); LC-MS (ESI+; 313 ([M+H]+)).

Workup

  1. filtrationthe rxn was filtered through a 0.45 μm
  2. filtrationfilter
  3. concentrationthen concentrated
  4. additionSatd NaHCO3 (10 mL) was added
  5. extractionthe product extracted into CHCl3 (2×2 mL)
  6. dry with materialThe soln was dried (MgSO4)
  7. filtrationfiltered through a plug of silica with an EtOAc
  8. washwash

Sources & evidence

ORD record
ord-8c2355e608ef4c958e15aa348f473b35
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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