Triethylamine → HCID 21075718, compound

HRID 1373927Notes

Reaction equation

HRID 1373927 reaction equation
[N:1]1([NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]=2[NH2:18])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:26]([O:28][CH2:29][C:30](Cl)=[O:31])[CH3:27]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:26]([O:28][CH2:29][C:30]([NH:18][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:8]=1[NH:7][N:1]1[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1)=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:31])[CH3:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 84189Ethoxyacetyl chlorideHCID 21075796HCID 21075796, compound

Product 1

HCID 21075718HCID 21075718, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N4-(morpholin-4-yl)quinoline-3,4-diamine (4.06 g, 16.6 mmol) in 50 mL of CH2Cl2 was treated with triethylamine (4.40 mL, 33.2 mmol) and cooled to 0° C. The solution was treated dropwise with ethoxyacetyl chloride (2.40 g, 17.4 mmol) and stirred under an atmosphere of nitrogen. The reaction mixture was allowed to slowly come to room temperature. After 2 d, the reaction mixture was concentrated under reduced pressure to yield a red semi-solid. The material was dissolved in CHCl3 and washed with water, 5% Na2CO3 solution and brine, dried over Na2SO4, filtered and dried to yield 2-ethoxy—N-{4-[(morpholin-4-yl)amino]quinolin-3-yl}acetamide (5.35 g) as a red/orange foam.

Workup

  1. customto slowly come to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customto yield a red semi-solid
  4. washwashed with water, 5% Na2CO3 solution and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-bef7b3cfaf914065a29683424e8ced7f
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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