Triethylamine → HCID 18951104, compound

HRID 1492509Notes

Reaction equation

HRID 1492509 reaction equation
C(N(CC)CC)C.Cl[C:9](OC(Cl)(Cl)Cl)=[O:10].[NH2:16][C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][CH:21]=2.[NH2:27][CH2:28][C:29]([N:31]([CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:30]>ClCCl.O>[N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[C:17]([NH:16][C:9](=[O:10])[NH:27][CH2:28][C:29]([N:31]([CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:30])[CH:18]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 113753-AminoquinolineHCID 18951114HCID 18951114, compound

Product 1

HCID 18951104HCID 18951104, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

1 g of triethylamine and 0.49 g of trichloromethyl chloroformate are added, at a temperature close to 0° C., to a solution of 0.72 g of 3-aminoquinoline in 30 cm3 of dichloromethane. The suspension obtained is stirred for 15 minutes at a temperature close to 0° C. and a solution of 1.3 g of tert-butyl 2-(2-amino-N-phenylacetamido)acetate in 10 cm3 of dichloromethane is then added. The reaction mixture is stirred for 3 hours at a temperature close to 20° C. and 20 cm3 of water are then added. The aqueous phase is separated off by decantation and then reextracted with twice 15 cm3 of 1,2-dichloroethane. The organic phases are combined, washed with twice 10 cm3 of water, dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The oil obtained is purified by chromatography on 50 g of silica (0.063-0.2 mm) contained in a column 1.5 cm in diameter [eluent: dichloromethane/methanol (98/2 by volume)], collecting 10-cm3 fractions. The fractions containing only the desired product are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization from ethyl acetate, 0.8 g of tert-butyl 2-{2-[3-(3-quinolyl)ureido]-N-phenylacetamido}acetate melting at 191° C. is obtained.

Workup

  1. customThe suspension obtained
  2. customclose to 0° C.
  3. stirringThe reaction mixture is stirred for 3 hours at a temperature
  4. customclose to 20° C.
  5. customThe aqueous phase is separated off by decantation
  6. washwashed with twice 10 cm3 of water
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  10. customThe oil obtained
  11. customis purified by chromatography on 50 g of silica (0.063-0.2 mm)
  12. customcollecting 10-cm3 fractions
  13. additionThe fractions containing only the desired product
  14. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  15. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-ef599304951b48c48417f15fc4884ef6
Source dataset
uspto-grants-1994_12
Patent number
US05374656

Reaction notes

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