HCID 67539976, compound → HCID 67537632, compound

HRID 1192434Notes

Reaction equation

HRID 1192434 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][N:8]=[C:7]2[N:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)([O-])=O>COCCO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][N:8]=[C:7]2[N:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1

Participants

4

Reactant 1

HCID 67539976HCID 67539976, compound

Product 1

HCID 67537632HCID 67537632, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80192-MethoxyethanolSolvent2×

Procedure

To a suspension of Pd/C (5% w/w, 800 mg, 0.38 mmol) in 100 mL 2-methoxyethanol (degassed with nitrogen prior to use) was added a solution of 4-(6-nitro-quinazolin-4-yl)-1-Boc-piperazine (4.0 g, 11.1 mmol) in 10 mL 2-methoxyethanol. A balloon of H2 was bubbled through the reaction mixture, and the reaction mixture was stirred at room temperature under an atmosphere of H2 for 13 hours. Celite was then added, and the reaction mixture was filtered through a pad of celite and rinsed with MeOH. The filtrate was concentrated, and the resulting oil was filtered through a short plug of silica gel with EtOAc. The resulting filtrate was concentrated to give 4-(6-amino-quinazolin-4-yl)-1-Boc-piperazine (3.47 g, 95%). LCMS (APCI+) m/z 330 [M+H]+. HPLC Rt 2.31 min.

Workup

  1. customdegassed with nitrogen
  2. customA balloon of H2 was bubbled through the reaction mixture
  3. additionCelite was then added
  4. filtrationthe reaction mixture was filtered through a pad of celite
  5. washrinsed with MeOH
  6. concentrationThe filtrate was concentrated
  7. filtrationthe resulting oil was filtered through a short plug of silica gel with EtOAc
  8. concentrationThe resulting filtrate was concentrated

Sources & evidence

ORD record
ord-3e82770a796949d9845a620f8e37b95e
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

Loading…