Benzyl (2S)-4-(4-amino-6,7-dimethoxy-2-quinazolinyl)-2-[(2-methyl-2-propanyl)carbamoyl]-1-piperazinecarboxylate → HCID 10739024, compound

HRID 1288836Notes

Reaction equation

HRID 1288836 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][N:19](C(OCC3C=CC=CC=3)=O)[C@H:18]([C:32]([NH:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:17]2)[N:3]=1>CCO.[Pd]>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][NH:19][C@H:18]([C:32]([NH:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:17]2)[N:3]=1

Participants

4

Reactant 1

HCID 6603904Benzyl (2S)-4-(4-amino-6,7-dimethoxy-2-quinazolinyl)-2-[(2-methyl-2-propanyl)carbamoyl]-1-piperazinecarboxylate

Product 1

HCID 10739024HCID 10739024, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (S)-1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-[(benzyloxy)carbonyl]-3-(1,1-dimethylethylamino)carbonyl piperazine (1.11 g, 2.124 mmol) and 10% Pd-C (111 mg, 10 weight %) in dry EtOH (8 mL) was evacuated under high vacuum and purged to a H2 balloon (14 h). The mixture was filtered through Celite (30 mm×30 mm), the filter cake washed with EtOH and concentrated in vacuo. PCTLC (SiO2, 4 mm, 0-10% CH3OH/CH2 Cl2) provided the title compound.

Workup

  1. custompurged to a H2 balloon (14 h)
  2. filtrationThe mixture was filtered through Celite (30 mm×30 mm)
  3. washthe filter cake washed with EtOH
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-14ae27e7170b478ba4f96aef44eb711d
Source dataset
uspto-grants-1998_05
Patent number
US05747490

Reaction notes

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