Triethylamine → HCID 67856646, compound

HRID 484432Notes

Reaction equation

HRID 484432 reaction equation
Cl.N[C@@H:3]1[C:12]2[C:7](=[CH:8][C:9]([Cl:14])=[CH:10][C:11]=2[Cl:13])[NH:6][C@@H:5]([C:15]([O:17][CH3:18])=[O:16])[CH2:4]1.Cl.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1.C([N:31](CC)CC)C>ClCCl>[Cl:13][C:11]1[CH:10]=[C:9]([Cl:14])[CH:8]=[C:7]2[C:12]=1[C@@H:3]([C:20]([C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)=[O:27])[CH2:4][C@H:5]([C:15]([O:17][CH3:18])=[O:16])[N:6]2[NH2:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 67690826HCID 67690826, compound

Product 1

HCID 67856646HCID 67856646, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of trans-4-amino-5,7-dichloro-2-methoxycarbonyl-1,2,3,4-tetrahydroquinoline hydrochloride (example 9a) (0.200 g, 0.642 mmol) and isonicotinoyl chloride hydrochloride (0.124 g, 0.706 mmol) in anhydrous dichloromethane (20 ml) under an atmosphere of nitrogen was added dry triethylamine (0.307 ml, 2.2 mmol) and the resulting mixture was stirred at room temperature for 1 h. The mixture was then evaporated to dryness in vacuo and the residue was partitioned between water (100 ml) and ethyl acetate (250 ml). The organic layer was separated, washed successively with water (3×100 ml), saturated sodium bicarbonate solution (1×100 ml), brine (1×100 ml), dried (MgSO4) and evaporated. The resulting solid was triturated with ethyl acetate and collected by filtration to give the title compound as colourless crystals (0.200 g) mp 200° C. (dec) δ (DMSO, 360 MHz) 1.82 (1H, ddd, J=13.2, 12.6 and 4.1 Hz, CHACHBHCCHD), 2.27 (1H, dm, J=13.2 Hz, CHACHBHCCHD), 3.72 (3H, s, CO2CH3), 4.07 (1H, dd, J=12.6 and 2.9 Hz, CHACHBHCCHD), 5.27 (1H, m, CHACHBHCCHDNHCO-), 6.70 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.91 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.97 (1H, s, ArNH), 7.77 (2H, dd, J=4.5 and 1.6 Hz, ArH), 8.70 (2H, dd, J=4.5 and 1.6 Hz, ArH), 9.02 (1H, d, J=7.1 Hz, -CHDNHCO-); m/e (CI+) 380 (M+1)+, 123 (100%).

Workup

  1. customThe mixture was then evaporated to dryness in vacuo
  2. customthe residue was partitioned between water (100 ml) and ethyl acetate (250 ml)
  3. customThe organic layer was separated
  4. washwashed successively with water (3×100 ml), saturated sodium bicarbonate solution (1×100 ml), brine (1×100 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe resulting solid was triturated with ethyl acetate
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-89e244abce304b7a9dc3007db1fbd03b
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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