1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 131730992, compound

HRID 2035524Notes

Reaction equation

HRID 2035524 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([F:32])[CH:31]=1)[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[N:10]=[CH:9][C:8]=1C(O)=O.Cl.C(N=C=NCCCN(C)C)C.O.O[N:47]1[C:51]2[CH:52]=CC=CC=2N=N1.C(N)C.C1C[O:62][CH2:61][CH2:60]1>CS(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([F:32])[CH:31]=1)[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)=[CH:16][CH:15]=2)[N:10]=[CH:9][C:8]=1[CH2:60][C:61]([NH:47][CH2:51][CH3:52])=[O:62]

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66726184Ethylamine tetrahydrofuranHCID 67412650HCID 67412650, compound

Product 1

HCID 131730992HCID 131730992, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

100 mg of 4-[(3,5-difluorobenzyl)amino]-6-[(4-morpholinophenyl)amino]pyridine-3-carboxylic acid was dissolved in 15 mL of dimethyl sulfoxide, to which 65.3 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 52.2 mg of 1-hydroxybenzotriazole monohydrate were added at room temperature, and stirred at the same temperature for 2 hours. After the reaction was over, 2 mL of 2 mol/L ethylamine-THF solution was added, stirred overnight at room temperature. Then water was added, extracted with chloroform, the extract was washed with saturated saline, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (chloroform:methanol=10:1) to obtain 13.9 mg (13%) of the title compound as a light brown solid.

Workup

  1. additionwere added at room temperature
  2. additionwas added
  3. stirringstirred overnight at room temperature
  4. extractionextracted with chloroform
  5. washthe extract was washed with saturated saline
  6. dry with materialdried on anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel thin layer chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-e9b2303cdc494b2bb0c1b6395b7c015f
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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