Tetrahydrofuran → HCID 15168525, compound

HRID 484435Notes

Reaction equation

HRID 484435 reaction equation
Cl.[NH2:2][CH:3]1[C:12]2[C:7](=[CH:8][C:9]([Cl:14])=[CH:10][C:11]=2[Cl:13])[NH:6][CH:5]([C:15]([O:17][CH3:18])=[O:16])[CH2:4]1.C(N(CC)CC)C.ON1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2N=N1.Cl.CN(C)CCCN=C=NCC.[O:48]1CC[CH2:50][CH2:49]1>>[Cl:13][C:11]1[CH:10]=[C:9]([Cl:14])[CH:8]=[C:7]2[C:12]=1[C@@H:3]([NH:2][C:49]([CH2:50][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:48])[CH2:4][C@H:5]([C:15]([O:17][CH3:18])=[O:16])[NH:6]2

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 197473812-Methoxycarbonyl-5,7-dichloro-4-amino-1,2,3,4-tetrahydroquinoline hydrochloride

Product 1

HCID 15168525HCID 15168525, compound

Procedure

To a suspension of 4-amino-5,7-dichloro-2-methoxycarbonyl-1,2,3,4-tetrahydroquinoline hydrochloride (example 9a) (3.0 g, 9.63 mmol) in anhydrous tetrahydrofuran (300 ml) under an atmosphere of nitrogen was added dry triethylamine (2.95 ml, 21.2 mmol) and the resulting mixture was stirred at room temperature for 0.5 h. To this suspension was added phenlyacetic acid (1.44 g, 10.6 mmol), 1-hydroxybenzotriazole (1.43 g, 10.6 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.03 g, 10.6 mmol) and stirring was continued for 65 h. The reaction mixture was concentrated in vacuo and the residue obtained was partitioned between ethyl acetate (1000 ml) and 1M aqueous citric acid (300 ml). The organic layer was collected, washed successively with 1M aqueous citric acid (1×300 ml), saturated sodium bicarbonate solution (2×300 ml) and brine (200 ml) then dried (MgSO4) and evaporated. The resulting crude product was recrystallised from methanol to give the title compound as colourless needles (2 crops, 3.26 g) identical in physical properties to the material obtained in example 34 step a.

Workup

  1. stirringstirring
  2. waitwas continued for 65 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue obtained
  5. customwas partitioned between ethyl acetate (1000 ml) and 1M aqueous citric acid (300 ml)
  6. customThe organic layer was collected
  7. washwashed successively with 1M aqueous citric acid (1×300 ml), saturated sodium bicarbonate solution (2×300 ml) and brine (200 ml)
  8. dry with materialthen dried (MgSO4)
  9. customevaporated
  10. customThe resulting crude product was recrystallised from methanol

Sources & evidence

ORD record
ord-9daab2237ea440a799047b6f0e5f61e0
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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