Diisopropylethylamine → [3-(4-Methoxyquinolin-2-ylamino)propyl]carbamic acid tert-butyl ester

HRID 2415125Notes

Reaction equation

HRID 2415125 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5](OS(C(F)(F)F)(=O)=O)[CH:4]=1.[NH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29].C(N(C(C)C)CC)(C)C>C(#N)C>[C:28]([O:27][C:26](=[O:32])[NH:25][CH2:24][CH2:23][CH2:22][NH:21][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 235256351,1,1-Trifluoromethanesulfonic acid 4-methoxyquinolin-2-yl ester

Product 1

HCID 57437795[3-(4-Methoxyquinolin-2-ylamino)propyl]carbamic acid tert-butyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,1,1-trifluoromethanesulfonic acid 4-methoxyquinolin-2-yl ester (4.51 g, 14.7 mmol), tert-butyl N-(3-aminopropyl)carbamate (3.07 g, 17.6 mmol), and diisopropylethylamine (3.84 ml, 22.0 mmol) in anhydrous acetonitrile (35 ml) was heated at reflux for 6 days. The solution was cooled to ambient temperature then evaporated under reduced pressure to an oil. It was taken into water (35 ml) then extracted into ethyl acetate. The extracts were dried (sodium sulfate) then concentrated to an oil. Column chromatography on silica (1:1 ethyl acetate/hexanes) gave [3-(4-methoxyquinolin-2-ylamino)propyl]carbamic acid tert-butyl ester (3.10 g, 64%) as a colorless oil that solidified on standing. [M+H]+ 332.

Workup

  1. temperatureat reflux for 6 days
  2. customthen evaporated under reduced pressure to an oil
  3. extractionthen extracted into ethyl acetate
  4. dry with materialThe extracts were dried (sodium sulfate)
  5. concentrationthen concentrated to an oil

Sources & evidence

ORD record
ord-8323fc7442294a118f810284484dc8cb
Source dataset
uspto-grants-2004_11
Patent number
US06818655B2

Reaction notes

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