Triethylamine → HCID 19598387, compound

HRID 1957404Notes

Reaction equation

HRID 1957404 reaction equation
ClC(OCC)=O.Br.[C:8]([C:11]1[CH:16]=[CH:15][C:14]([N:17]([S:34]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)(=[O:36])=[O:35])[C:18]([C:20]2[C:21]3[C:26]([N:27]=[C:28]4[C:33]=2[CH:32]=[CH:31][CH:30]=[CH:29]4)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:19])=[CH:13][CH:12]=1)([OH:10])=[O:9].C(N(CC)CC)C.Br.COC1C=CC(N(S(C2C=CC(CCCCC(O)=O)=CC=2)(=O)=O)C(C2C3C(N=C4C=2C=CC=C4)=CC=CC=3)=O)=CC=1.O[N:94]1[C:98](=[O:99])[CH2:97][CH2:96][C:95]1=[O:100]>O1CCCC1>[C:95]1(=[O:100])[N:94]([O:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]([N:17]([S:34]([C:37]3[CH:38]=[CH:39][C:40]([CH3:43])=[CH:41][CH:42]=3)(=[O:35])=[O:36])[C:18]([C:20]3[C:33]4[C:28]([N:27]=[C:26]5[C:21]=3[CH:22]=[CH:23][CH:24]=[CH:25]5)=[CH:29][CH:30]=[CH:31][CH:32]=4)=[O:19])=[CH:15][CH:16]=2)=[O:10])[C:98](=[O:99])[CH2:97][CH2:96]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 80170N-HydroxysuccinimideHCID 14459520HCID 14459520, compoundHCID 19598388HCID 19598388, compound

Product 1

HCID 19598387HCID 19598387, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.11 g (1 mmol) of ethyl chloroformate is added, while stirring at -15° C., to a solution of 0.57 g (1 mmol) of N-(4-carboxyphenyl)-N-(4-toluenesulfonyl)acridine-9-carboxamide hydrobromide and 0.21 g (2 mmol) of triethylamine in 25 ml of anhydrous tetrahydrofuran. The mixture is stirred at the same temperature for 1 hour and then 0.12 9 (1 mmol) of N-hydroxysuccinimide is added. After a further hour, the mixture is left to stand at room temperature for 15 hours. It is evaporated in vacuo, the residue is taken up in ethyl acetate, and the solution is washed with water, sodium bicarbonate solution and water and dried over sodium sulfate. Evaporation yields 0.42 g (70.8% of theory) of the desired product.

Workup

  1. waitAfter a further hour
  2. waitthe mixture is left
  3. waitto stand at room temperature for 15 hours
  4. customIt is evaporated in vacuo
  5. washthe solution is washed with water, sodium bicarbonate solution and water
  6. dry with materialdried over sodium sulfate
  7. customEvaporation

Sources & evidence

ORD record
ord-888bb95ca5a34fa7a1a515f44bcacb92
Source dataset
uspto-grants-1998_07
Patent number
US05783696

Reaction notes

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