1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 15886884, compound

HRID 651577Notes

Reaction equation

HRID 651577 reaction equation
[CH:1]1[C:6]2[C:7]3NC4C([C:15]=3[CH:16]([C:18]([OH:20])=O)[S:17][C:5]=2[CH:4]=[CH:3][CH:2]=1)=CC=CC=4.[C:21]([O:25][C:26]([CH2:28][CH2:29][CH2:30][NH:31][CH2:32][CH2:33][NH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[O:27])([CH3:24])([CH3:23])[CH3:22].O.O[N:43]1[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=2N=N1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[C:21]([O:25][C:26]([CH2:28][CH2:29][CH2:30][NH:31][CH2:32][CH2:33][N:34]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:18]([CH:16]1[C:15]2[C:46]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[NH:43][C:7]=2[C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[S:17]1)=[O:20])=[O:27])([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 15886891HCID 15886891, compoundHCID 15886892HCID 15886892, compound

Product 1

HCID 15886884HCID 15886884, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 844 mg of 6,11-dihydro-5-thia-11-aza-benzo[a]fluoren-6-carboxylic acid and 1.66 g of N-2-(N-t-butoxycarbonylpropylamino)ethyl-hexylamine in 44 ml of dichloromethane were added 552 mg of 1-hydroxybenzotriazole monohydrate and 863 mg of N-ethyl-N′-dimethylaminopropylcarbodiimide hydrochloride, followed by stirring at room temperature overnight. The reaction solution, after concentration under reduced pressure, was dissolved in ethyl acetate, washed with water 5% aqueous potassium bisulfate solution, 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 subjected to flash chromatography (silica gel; Chromatorex NHDM1020 produced by Fuji-Davison Chemical Co., developing solvent; hexane-ethyl acetate=2:1-3:2) to give 1.35 g of N-2-(N-t-butoxycarbonylpropylamino)ethyl-N-hexyl-6,11-dihydro-5-thia-11-aza-benzo[a]fluoren-6-carboxamide as an amorphous substance.

Workup

  1. concentrationThe reaction solution, after concentration under reduced pressure
  2. dissolutionwas dissolved in ethyl acetate
  3. washwashed with water 5% aqueous potassium bisulfate solution
  4. dry with materiala saturated aqueous sodium bicarbonate solution and a 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 subjected to flash chromatography (silica gel; Chromatorex NHDM1020 produced by Fuji-Davison Chemical Co., developing solvent; hexane-ethyl acetate=2:1-3:2)

Sources & evidence

ORD record
ord-f617b01d60e3471ea31ce28aa07e3dd2
Source dataset
uspto-grants-2001_08
Patent number
US06281355B1

Reaction notes

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