Diisopropylethylamine → (S)-3-Methyl-2-[3-(2-methyl-quinolin-4-yl)-ureido]-butyric acid

HRID 2223716Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[C:10]([NH:12][C:13](NC2C3C(=CC=CC=3)N=C(C)C=2)=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl.C[O:29][C:30](=[O:36])[C@H:31]([CH:33]([CH3:35])[CH3:34])[NH2:32].CCN(C(C)C)C(C)C>CO>[CH3:34][CH:33]([CH3:35])[C@H:31]([NH:32][C:13]([NH:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([CH3:1])[CH:11]=1)=[O:14])[C:30]([OH:29])=[O:36]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 1,3-bis-(2-methyl-quinolin-4-yl)-urea (342.4 mg, 1 mmol), valin methyl ester hydrochloride (167.6 mg, 1 mmol) and DIPEA (0.34 mL, 2 mmol) in MeOH (10 mL) is heated at 80° C. for 15 h. The solvent is evaporated and the residue is dissolved in 6N aqueous HCl (6 mL). The reaction mixture is heated at 90° C. for 12 h. Evaporation and purification by preparative HPLC provides the title compound.

Workup

customThe solvent is evaporated
dissolutionthe residue is dissolved in 6N aqueous HCl (6 mL)
temperatureThe reaction mixture is heated at 90° C. for 12 h
customEvaporation and purification by preparative HPLC

Sources & evidence

ORD record: ord-193e665612ec4b8fbba5690dc79fd78b
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375227B2

Reaction notes

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