Triethylamine → HCID 136121360, compound

HRID 2079320Notes

Reaction equation

HRID 2079320 reaction equation
C(O[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:24])[C@H:18]([OH:23])[CH2:19][C:20](=[O:22])[CH3:21])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.ClC1[C:35]2[C:30](=[CH:31][C:32]([CH3:36])=[CH:33][CH:34]=2)[N:29]=[C:28]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[OH:43])[N:27]=1.C(N(CC)CC)C>[Pd].CO>[OH:23][C@H:18]([CH2:19][C:20](=[O:22])[CH3:21])[C:17]([N:14]1[CH2:13][CH2:12][N:11]([C:9]2[C:35]3[C:30](=[CH:31][C:32]([CH3:36])=[CH:33][CH:34]=3)[N:29]=[C:28]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[OH:43])[N:27]=2)[CH2:16][CH2:15]1)=[O:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 58010827HCID 58010827, compoundHCID 1361050322-(4-Chloro-7-methylquinazolin-2-yl)-phenol

Product 1

HCID 136121360HCID 136121360, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-((R)-2-hydroxy-4-oxo-pentanoyl)-piperazine-1-carboxylic acid benzyl ester (0.13 g, 0.39 mmol) and MeOH (4 mL) was stirred with 10 mg of Pd/C (10% wt Pd on carbon) under H2 atmosphere at ambient pressure overnight. After filtration and evaporation of the solvent, the residue was taken up in CH2Cl2, and 2-(4-chloro-7-methylquinazolin-2-yl)phenol (0.11 g, 0.39 mmol) and triethylamine (0.11 mL, 0.78 mmol) were added. The reaction mixture was stirred at room temperature overnight, washed with water, dried over Na2SO4, and concentrated. Purification via silica gel chromatography using 0-10% MeOH/CH2Cl2 provided (R)-2-hydroxy-1-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)pentan-1,4-dione as a yellow solid (91 mg, 54%). LC/MS: m/z 435.5 (M+H)+ at 2.13 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))yl)piperazin-1-yl)pentan-1,4-dione as a yellow solid (91 mg, 54%). LC/MS: m/z 435.5 (M+H)+ at 2.13 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. filtrationAfter filtration and evaporation of the solvent
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-d5db8bd099ac4220a91b593917cffd46
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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