Triethylamine → HCID 11733337, compound

HRID 1609401Notes

Reaction equation

HRID 1609401 reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[CH2:18][CH2:17][N:9]2[C:10]3[C:15]([CH:16]=[C:8]2[CH2:7]1)=[CH:14][CH:13]=[CH:12][CH:11]=3)(=[O:3])[CH3:2].[C:19](Cl)(=O)[C:20](Cl)=[O:21].Cl.[CH3:26][N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([CH2:36][C:37](=[NH:42])[O:38]C(C)C)=[CH:28]1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[C:1]([O:4][CH2:5][C@H:6]1[CH2:18][CH2:17][N:9]2[C:10]3[C:15]([C:16]([C:19]4[C:20](=[O:21])[NH:38][C:37](=[O:42])[C:36]=4[C:29]4[C:30]5[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=5)[N:27]([CH3:26])[CH:28]=4)=[C:8]2[CH2:7]1)=[CH:14][CH:13]=[CH:12][CH:11]=3)(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 65578Oxalyl chlorideHCID 10399532HCID 10399532, compoundHCID 22907276Isopropyl 1-methyl-3-indoleacetimidate hydrochloride

Product 1

HCID 11733337HCID 11733337, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A stirred solution of 2.43 g (10 mmol) of (S)-8-(acetoxymethyl)-6,7,8,9-tetrahydropyrido [1,2-a]indole (prepared as described in Example 2) in 15 ml of dichloromethane was treated at 0° C. with a solution of 1.27 g (10 mmol) of oxalyl chloride in 5 ml of dichloromethane. The solution was stirred for 15 minutes and then treated with 2.67 g (10 mmol) of isopropyl 1-methyl-3-indoleacetimidate hydrochloride (prepared as described in Example 1) followed by 10 ml of dichloromethane. The mixture obtained was treated with 5.05 g (10 mmol) of triethylamine, allowed to warm to room temperature and stirred for 2 hours. The mixture was then washed with water and the organic layer was dried over magnesium sulfite and evaporated to dryness. The residue was dissolved in 30 ml of pyridine, cooled in ice and treated dropwise with 2.10 g (10 mmol) of trifluoroacetic anhydride over 2-3 minutes. After 15 minutes, the solvent was evaporated in vacuo and the residue was partitioned between dichloromethane and 2M hydrochloric acid. The organic layer was washed with water and saturated sodium bicarbonate solution, dried over magnesium sulfite and evaporated. The residue was triturated with 30 ml of methanol and the solid was removed by filtration. The product was washed with methanol and dried to give 2.45 g (52%) of (S)-3-[8-(acetoxymethyl)-6,7,8,9-tetrahydro-pyrido [1,2-a]indol- 10-yl]-4(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione in the form of a red solid of melting point 238°-241° C.

Workup

  1. customThe mixture obtained
  2. stirringstirred for 2 hours
  3. washThe mixture was then washed with water
  4. dry with materialthe organic layer was dried over magnesium sulfite
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in 30 ml of pyridine
  7. temperaturecooled in ice
  8. waitAfter 15 minutes
  9. customthe solvent was evaporated in vacuo
  10. customthe residue was partitioned between dichloromethane and 2M hydrochloric acid
  11. washThe organic layer was washed with water and saturated sodium bicarbonate solution
  12. dry with materialdried over magnesium sulfite
  13. customevaporated
  14. customThe residue was triturated with 30 ml of methanol
  15. customthe solid was removed by filtration
  16. washThe product was washed with methanol
  17. customdried

Sources & evidence

ORD record
ord-2abc4f8bd9574ca9acb2d92f15e4817b
Source dataset
uspto-grants-1995_03
Patent number
US05399712

Reaction notes

Loading…