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

HRID 2223696Notes

Reaction equation

HRID 2223696 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][CH:8]1[CH2:12][CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:15][CH2:16][NH:17][C:18]([NH:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=[C:23]([CH3:31])[CH:22]=1)=[O:19].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:13])[NH:7][CH:8]1[CH2:12][CH2:11][N:10]([CH2:15][CH2:16][NH:17][C:18]([NH:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=[C:23]([CH3:31])[CH:22]=2)=[O:19])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 1859152-NaphthylalanineHCID 516892Sodium BicarbonateHCID 23443661-(2-Chloroethyl)-3-(2-methylquinolin-4-yl)ureaHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamate

Product 1

HCID 59715918(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 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-cd70f26a67dc4766a687a8fbd93d3f8f
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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