HCID 15886884, compound → HCID 15886885, compound

HRID 651578Notes

Reaction equation

HRID 651578 reaction equation
C(OC([CH2:8][CH2:9][CH2:10][NH:11][CH2:12][CH2:13][N:14]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:15]([CH:17]1[C:29]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][C:21]=2[C:20]2[CH:30]=[CH:31][CH:32]=[CH:33][C:19]=2[S:18]1)=[O:16])=O)(C)(C)C>C(O)=O>[CH2:10]([NH:11][CH2:12][CH2:13][N:14]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:15]([CH:17]1[C:29]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][C:21]=2[C:20]2[CH:30]=[CH:31][CH:32]=[CH:33][C:19]=2[S:18]1)=[O:16])[CH2:9][CH3:8]

Participants

3

Reactant 1

HCID 15886884HCID 15886884, compound

Product 1

HCID 15886885HCID 15886885, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

In 4.3 ml of 99% formic acid was stirred 600 mg of N-2-(N-t-butoxycarbonylpropylamino)ethyl-N-hexyl-6,11-dihydro-5-thia-11-aza-benzo[a]fluoren-6-carboxamide for 5 hours. The reaction solution, after concentration under reduced pressure, was dissolved in ethyl acetate, washed with a saturated aqueous sodium bicarbonate solution and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate to give 406 mg of N-2-(propylamino)ethyl-N-hexyl-6,11-dihydro-5-thia-11-aza-benzo[a]fluoren-6-carboxamide.

Workup

  1. concentrationThe reaction solution, after concentration under reduced pressure
  2. dissolutionwas dissolved in ethyl acetate
  3. washwashed with a saturated aqueous sodium bicarbonate solution
  4. dry with materiala saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  5. customAfter removal of the drying agent
  6. filtrationby filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-58375e7f9b1541ab9c466be3c15064b7
Source dataset
uspto-grants-2001_08
Patent number
US06281355B1

Reaction notes

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