2-Naphthylalanine → Methyl-(1-{2-[3-(2-methyl-quinolin-4-yl)-ureido]-ethyl}-pyrrolidin-3-yl)-carbamic acid tert-butyl ester

HRID 2223694Notes

Reaction equation

HRID 2223694 reaction equation
[C:1]([O:5][C:6](=[O:14])[N:7]([CH3:13])[CH:8]1[CH2:12][CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:16][CH2:17][NH:18][C:19]([NH:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=[C:24]([CH3:32])[CH:23]=1)=[O:20].C([O-])(O)=O.[Na+].N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1>C1COCC1>[C:1]([O:5][C:6](=[O:14])[N:7]([CH3:13])[CH:8]1[CH2:12][CH2:11][N:10]([CH2:16][CH2:17][NH:18][C:19]([NH:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[C:24]([CH3:32])[CH:23]=2)=[O:20])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 1859152-NaphthylalanineHCID 516892Sodium BicarbonateHCID 23443661-(2-Chloroethyl)-3-(2-methylquinolin-4-yl)ureaHCID 27614043-(N-tert-Butoxycarbonyl-N-methylamino)pyrrolidine

Product 1

HCID 59715909Methyl-(1-{2-[3-(2-methyl-quinolin-4-yl)-ureido]-ethyl}-pyrrolidin-3-yl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl-pyrrolidin-3-yl-carbamic acid tert-butyl ester (10 mmol), 1-(2-chloro-ethyl)-3-(2-methyl-quinolin-4-yl)-urea (10 mmol), NaHCO3 (20 mmol), Nal (0.5 mmol), and THF (70 mL) is stirred in a sealed vessel at 70° C. for 6 d. The reaction mixture is filtered, evaporated to dryness, and the residue is purified by preparative HPLC to provide the title compound.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customevaporated to dryness
  3. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-0c2153306fe145dd8438a4cfac13ed62
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

Loading…