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

HRID 606040Notes

Reaction equation

HRID 606040 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][C:22]#[CH:23])[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][C:22]#[CH:23])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84189Ethoxyacetyl chlorideHCID 862475812-chloro-N4-prop-2-ynylquinoline-3,4-diamine

Product 1

HCID 86247582N-[2-chloro-4-(prop-2-ynylamino)quinolin-3-yl]-2-ethoxyacetamideYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethoxyacetyl chloride (89%, 28 g, 0.20 mol) was added dropwise to a solution of 2-chloro-N4-prop-2-ynylquinoline-3,4-diamine (43.5 g, 0.188 mol) and triethylamine (39 mL, 0.28 mol) in dichloromethane (600 mL) at 6° C. After two hours, the reaction mixture was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate. The aqueous layer was back-extracted with dichloromethane three times. The organic layers were combined and washed twice with water and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting brown solid was triturated with toluene with heating. A fine tan solid was isolated by filtration, rinsed with diethyl ether, and dried to yield N-[2-chloro-4-(prop-2-ynylamino)quinolin-3-yl]-2-ethoxyacetamide (47.2 g).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate
  2. extractionThe aqueous layer was back-extracted with dichloromethane three times
  3. washwashed twice with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting brown solid was triturated with toluene
  8. temperaturewith heating
  9. customA fine tan solid was isolated by filtration
  10. washrinsed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-9460237b00024437a28352fe8d20981e
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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