1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 68465430, compound

HRID 503012Notes

Reaction equation

HRID 503012 reaction equation
C1C=C2[N:7]=NN(O)C2=CC=1.O.CCN=C=NCCCN(C)C.Cl.O.N.[NH:26]([C:33]([C:36]1[N:37]([CH3:50])[C:38]([C:41]2[CH:49]=[CH:48][C:44]([C:45](O)=[O:46])=[CH:43][CH:42]=2)=[N:39][N:40]=1)([CH3:35])[CH3:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C.C1COCC1>[NH:26]([C:33]([C:36]1[N:37]([CH3:50])[C:38]([C:41]2[CH:42]=[CH:43][C:44]([C:45]([NH2:7])=[O:46])=[CH:48][CH:49]=2)=[N:39][N:40]=1)([CH3:35])[CH3:34])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 12896473Azane;hydrateHCID 68467030HCID 68467030, compound

Product 1

HCID 68465430HCID 68465430, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

HOBt hydrate (82 mg), WSC hydrochloride (103 mg), and ammonia water (33 μl) were added to a THF (1 ml) and DMF (1 ml) solution of 4-[5-(1-anilino-1-methylethyl)-4-methyl-4H-1,2,4-triazol-3-yl]benzoic acid (150 mg) at room temperature, followed by stirring at the same temperature overnight. After most of the solvent was removed by evaporation under reduced pressure, water was added thereto and the whole was extracted four times with ethyl acetate. The organic layer washed with brine, dried over anhydrous magnesium sulfate, and filtered, and then the solvent was removed by evaporation. Ethyl acetate was added to the resulting white crystals, which was filtered and washed with ethyl acetate to obtain 120 mg of 4-[5-(1-anilino-1-methylethyl)-4-methyl-4H-1,2,4-triazol-3-yl]benzamide (white crystals).

Workup

  1. customAfter most of the solvent was removed by evaporation under reduced pressure, water
  2. additionwas added
  3. extractionthe whole was extracted four times with ethyl acetate
  4. washThe organic layer washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed by evaporation
  8. additionEthyl acetate was added to the resulting white crystals, which
  9. filtrationwas filtered
  10. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-078bfe09e082460fbbf2f476496f8358
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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