Triethylamine → N-[2-chloro-4-(pent-4-ynylamino)quinolin-3-yl]-2-ethoxyacetamide

HRID 606052Notes

Reaction equation

HRID 606052 reaction equation
[CH2:1]([O:3][CH2:4][C:5](Cl)=[O:6])[CH3:2].[Cl:8][C:9]1[C:18]([NH2:19])=[C:17]([NH:20][CH2:21][CH2:22][CH2:23][C:24]#[CH:25])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.C(N(CC)CC)C>ClCCl>[Cl:8][C:9]1[C:18]([NH:19][C:5](=[O:6])[CH2:4][O:3][CH2:1][CH3:2])=[C:17]([NH:20][CH2:21][CH2:22][CH2:23][C:24]#[CH:25])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84189Ethoxyacetyl chloride2×HCID 862475962-chloro-N4-pent-4-ynylquinoline-3,4-diamine

Product 1

HCID 86247598N-[2-chloro-4-(pent-4-ynylamino)quinolin-3-yl]-2-ethoxyacetamideYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethoxyacetyl chloride (96%, 4.40 g, 34.3 mmol) was added to a 6° C. solution of 2-chloro-N4-pent-4-ynylquinoline-3,4-diamine (8.10 g, 31.2 mmol) and triethylamine (6.50 mL, 46.8 mmol) in dichloromethane (100 mL). Additional ethoxyacetyl chloride (3.0 g) was added after 45 minutes until all the starting material had been consumed. The solution was diluted with dichloromethane and washed with saturated aqueous potassium carbonate, water, and brine, dried over potassium carbonate, filtered, and concentrated to afford N-[2-chloro-4-(pent-4-ynylamino)quinolin-3-yl]-2-ethoxyacetamide as a pale yellow solid (10.23 g).

Workup

  1. customhad been consumed
  2. additionThe solution was diluted with dichloromethane
  3. washwashed with saturated aqueous potassium carbonate, water, and brine
  4. dry with materialdried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dd71ec09450d4742a6287171e06ceac9
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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