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Silica → 3-(2-Amino-6-benzyl-4H-quinazolin-3-yl)-N-cyclohexyl-N-methyl-propionamide

HRID 2088817
Notes
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Reaction equation

HRID 2088817 reaction equation
[NH2:1][C:2]1[N:11]([CH2:12][CH2:13][C:14]([N:16]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH3:17])=[O:15])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:24](O)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:8]=2)[N:3]=1.O=[Si]=O>CO.Cl.CC(O)C.[Pd]>[NH2:1][C:2]1[N:11]([CH2:12][CH2:13][C:14]([N:16]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH3:17])=[O:15])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:8]=2)[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 24261SilicaHCID 586251343-[2-Amino-6-(hydroxy-phenyl-methyl)-4H-quinazolin-3-yl]-N-cyclohexyl-N-methyl-propionamide

Product 1

HCID 586250563-(2-Amino-6-benzyl-4H-quinazolin-3-yl)-N-cyclohexyl-N-methyl-propionamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent
HCID 21912024
Isopropanol hydrochloride
Solvent

Procedure

A mixture of 3-[2-amino-6-(hydroxy-phenyl-methyl)-4H-quinazolin-3-yl]-N-cyclohexyl-N-methyl-propionamide (0.0012 mol) in methanol (40 mL) and HCl/2-propanol (0.5 mL) was hydrogenated at 50° C. with 10% Pd/C (0.4 g) as a catalyst. After uptake of H2 (1 equiv.), the reaction mixture was filtered over Dicalite and the solvent was evaporated. The residue was triturated under diisopropyl ether, then the resulting solids were filtered off and dried to yield the title compound as a solid.

Workup

  1. customthe solvent was evaporated
  2. customThe residue was triturated under diisopropyl ether
  3. filtrationthe resulting solids were filtered off
  4. customdried

Sources & evidence

ORD record
ord-60a115b413d24ca589afe9ff78005214
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08436006B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes