Triethylamine → 2-chloro-4-[4-((R)-2-hydroxy-4-methyl-pentanoyl)-piperazin-1-yl]-quinazoline-7-carboxylic acid

HRID 2079272Notes

Reaction equation

HRID 2079272 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][C:6]([C:13]([OH:15])=[O:14])=[CH:7][CH:8]=2)[N:3]=1.[OH:16][C@H:17]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[N:11]=[C:10]([N:23]2[CH2:22][CH2:21][N:20]([C:18](=[O:19])[C@H:17]([OH:16])[CH2:26][CH:27]([CH3:28])[CH3:29])[CH2:25][CH2:24]2)[C:9]2[C:4](=[CH:5][C:6]([C:13]([OH:15])=[O:14])=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 204913512,4-Dichloroquinazoline-7-carboxylic acidHCID 59216548(R)-2-hydroxy-4-methyl-1-(piperazin-1-yl)pentan-1-one

Product 1

HCID 580108202-chloro-4-[4-((R)-2-hydroxy-4-methyl-pentanoyl)-piperazin-1-yl]-quinazoline-7-carboxylic acidYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,4-dichloroquinazoline-7-carboxylic acid (0.45 g, 1.9 mmol) in CH2Cl2 (20 mL) was added (R)-2-hydroxy-4-methyl-1-piperazin-1-yl-pentan-1-one (0.37 g, 1.9 mmol) and triethylamine (0.52 mL, 3.7 mmol). The reaction mixture was stirred overnight at room temperature and then purified via silica gel chromatography using 0-10% MeOH/CH2Cl2 to obtain 2-chloro-4-[4-((R)-2-hydroxy-4-methyl-pentanoyl)-piperazin-1-yl]-quinazoline-7-carboxylic acid (0.58 g, 77%). LC/MS: m/z 407.3 (M+H)+ at 2.44 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. custompurified via silica gel chromatography

Sources & evidence

ORD record
ord-b95ffed30438441188f5b3d0e5273ccd
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

Loading…