1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 58236955, compound

HRID 1188960Notes

Reaction equation

HRID 1188960 reaction equation
[F:1][C:2]1[C:10]([OH:11])=[C:9]2[C:5]([CH:6]=[C:7]([C:12](O)=[O:13])[NH:8]2)=[CH:4][C:3]=1[O:15][C:16]1[CH:17]=[N:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=1.[NH4+].O[N:28]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[F:1][C:2]1[C:10]([OH:11])=[C:9]2[C:5]([CH:6]=[C:7]([C:12]([NH2:28])=[O:13])[NH:8]2)=[CH:4][C:3]=1[O:15][C:16]1[CH:17]=[N:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 58236987HCID 58236987, compound

Product 1

HCID 58236955HCID 58236955, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled and stirred mixture of 6-fluoro-7-hydroxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylic acid (2.5 g) in N,N-dimethylformamide (30 mL) were added 1-hydroxybenzotriazole ammonium salt (1.25 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.57 g). After stirred at 4° C. to room temperature for 15 h, the reaction mixture was partitioned between ethyl acetate and aqueous citric acid solution. The organic layer was washed successively with aqueous sodium hydrogen carbonate and brine, dried (MgSO4), filtered, and concentrated to give a light brown solid, which was washed with tetrahydrofuran-ethyl acetate to give the title compound (0.55 g, 22%) as a light pink solid. MS 366 (MH+).

Workup

  1. stirringAfter stirred at 4° C. to room temperature for 15 h
  2. customthe reaction mixture was partitioned between ethyl acetate and aqueous citric acid solution
  3. washThe organic layer was washed successively with aqueous sodium hydrogen carbonate and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a light brown solid, which
  8. washwas washed with tetrahydrofuran-ethyl acetate

Sources & evidence

ORD record
ord-cd3eaa7125224ea49c5cfbf0a9b67c15
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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