Ethoxyacetyl chloride → Tert-butyl 2-({2-chloro-3-[(ethoxyacetyl)amino]quinolin-4-yl}amino)ethylcarbamate

HRID 606065Notes

Reaction equation

HRID 606065 reaction equation
[CH2:1]([O:3][CH2:4][C:5](Cl)=[O:6])[CH3:2].[NH2:8][C:9]1[C:10]([Cl:30])=[N:11][C:12]2[C:17]([C:18]=1[NH:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:16][CH:15]=[CH:14][CH:13]=2>C(#N)C>[Cl:30][C:10]1[C:9]([NH:8][C:5](=[O:6])[CH2:4][O:3][CH2:1][CH3:2])=[C:18]([NH:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

Participants

4

Reactant 2

HCID 84189Ethoxyacetyl chlorideHCID 86616882Tert-butyl 2-[(3-amino-2-chloroquinolin-4-yl)amino]ethylcarbamate

Product 1

HCID 86616883Tert-butyl 2-({2-chloro-3-[(ethoxyacetyl)amino]quinolin-4-yl}amino)ethylcarbamateYield 93.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of ethoxyacetyl chloride (857 mg, 6.99 mmol) in acetonitrile (5 mL) was added to solution of tert-butyl 2-[(3-amino-2-chloroquinolin-4-yl)amino]ethylcarbamate (2.14 g, 6.35 mmol) in acetonitrile (20 mL). After five minutes, the solution was cooled in an ice bath and a white precipitate began to form. After one hour, the precipitate was isolated by filtration and dried under vacuum to afford the hydrochloride salt of tert-butyl 2-({2-chloro-3-[(ethoxyacetyl)amino]quinolin-4-yl}amino)ethylcarbamate (2.50 g).

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. customto form
  3. waitAfter one hour
  4. customthe precipitate was isolated by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-87c4883a99a14edc9dbb2b0855d5d17d
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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