Triethylamine → (R)-1-(4-(6-bromo-2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4-methylpentan-1-one

HRID 2079297Notes

Reaction equation

HRID 2079297 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])[N:6]=[C:5]2Cl.[OH:20][C@H:21]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])[N:6]=[C:5]2[N:27]1[CH2:26][CH2:25][N:24]([C:22](=[O:23])[C@H:21]([OH:20])[CH2:30][CH:31]([CH3:32])[CH3:33])[CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 59216548(R)-2-hydroxy-4-methyl-1-(piperazin-1-yl)pentan-1-oneHCID 1361215002-(6-Bromo-4-chloroquinazolin-2-yl)phenol

Product 1

HCID 136121577(R)-1-(4-(6-bromo-2-(2-hydroxyphenyl)quinazolin-4-yl)piperazin-1-yl)-2-hydroxy-4-methylpentan-1-oneYield 36.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6-bromo-4-chloro-2-(2-hydroxyphenyl)quinazoline (75 mg, 0.22 mmol), (R)-2-hydroxy-4-methyl-1-piperazin-1-yl-pentan-1-one (60 mg, 0.3 mmol), triethylamine (42 μL, 0.3 mmol), and CH2Cl2 (2 mL) was stirred at room temperature overnight. After diluting with CH2Cl2, the reaction mixture was washed with H2O, dried over Na2SO4, and concentrated. The crude material was purified by silica gel chromatography using 0-10% MeOH/CH2Cl2 to give (R)-1-{4-[6-bromo-2-(2-hydroxyphenyl)-quinazolin-4-yl]-piperazin-1-yl}-2-hydroxy-4-methyl-pentan-1-one (40 mg, 36%).

Workup

  1. washthe reaction mixture was washed with H2O
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9c42ba043bf344a8a9afb10cf133852d
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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