1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 58149876, compound

HRID 2192500Notes

Reaction equation

HRID 2192500 reaction equation
Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.[Cl:23][C:24]1[CH:25]=[C:26]([C:34]([OH:36])=O)[CH:27]=[N:28][C:29]=1[O:30][CH:31]([CH3:33])[CH3:32].O[NH:38][C:39](=[NH:58])[C:40]1[CH:49]=[CH:48][CH:47]=[C:46]2[C:41]=1[CH:42]=[CH:43][N:44]=[C:45]2[CH2:50][CH2:51][CH2:52][C:53]([O:55][CH2:56][CH3:57])=[O:54].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:23][C:24]1[CH:25]=[C:26]([C:34]2[O:36][N:58]=[C:39]([C:40]3[CH:49]=[CH:48][CH:47]=[C:46]4[C:41]=3[CH:42]=[CH:43][N:44]=[C:45]4[CH2:50][CH2:51][CH2:52][C:53]([O:55][CH2:56][CH3:57])=[O:54])[N:38]=2)[CH:27]=[N:28][C:29]=1[O:30][CH:31]([CH3:32])[CH3:33]

Participants

7

Reactant 5

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724141Tetrabutylammonium FluorideHCID 180705825-Chloro-6-isopropoxynicotinic acidHCID 178418300HCID 178418300, compoundHCID 178471277HCID 178471277, compound

Product 1

HCID 58149876HCID 58149876, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI; 0.77 g) and hydroxybenzotriazole (HOBt; 0.54 g) were added sequentially to a solution of 5-chloro-6-[(1-methylethyl)oxy]-3-pyridinecarboxylic acid (WO 2008128951; 0.43 g) in THF (20 mL) at room temperature and the resulting solution was stirred for 30 minutes. Ethyl 4-{5-[(hydroxyamino)(imino)methyl]-1-isoquinolinyl}butanoate (D43; 0.6 g) was added and the resulting suspension was stirred at room temperature for 1 hour. Tetra-n-butylammonium fluoride (TBAF; 1.57 g) was added to the reaction mixture and the resulting solution was heated to reflux for overnight. The solvent was evaporated in vacuo and the residue was dissolved in ethyl acetate (50 ml). The organic phase was washed with water and brine, then dried over anhydrous sodium sulphate. The dried solution was filtered and the filtrate was concentrated. The residue was purified by column chromatography to give the title compound (0.36 g). δH (CDCl3, 400 MHz): 1.29 (3H, t), 1.47 (6H, d), 2.25 (2H, m), 2.54 (2H, m), 3.50 (2H, m), 4.18 (2H, q), 5.52 (1H, m), 7.81 (1H, dd), 8.45 (1H, d), 8.53 (1H, d), 8.61 (2H, m), 8.79 (1H, d), 8.94 (1H, d). MS (ES): C25H25ClN4O4 requires 480. found 481.2 (M+H+).

Workup

  1. stirringthe resulting suspension was stirred at room temperature for 1 hour
  2. temperaturethe resulting solution was heated
  3. temperatureto reflux for overnight
  4. customThe solvent was evaporated in vacuo
  5. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. filtrationThe dried solution was filtered
  9. concentrationthe filtrate was concentrated
  10. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b58c4f35908c40c2ac430f5a37f3f4a0
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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