1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59829844, compound

HRID 1947189Notes

Reaction equation

HRID 1947189 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:17])[NH:15][NH2:16])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH:18]([C:21]1[C:22]([O:34][CH2:35][O:36][CH3:37])=[CH:23][C:24]([O:30][CH2:31][O:32][CH3:33])=[C:25]([CH:29]=1)[C:26](O)=[O:27])([CH3:20])[CH3:19].O.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(=O)([O-])O.[Na+]>CN(C)C=O.C(OCC)(=O)C.CN1CCCC1=O>[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14](=[O:17])[NH:15][NH:16][C:26](=[O:27])[C:25]3[CH:29]=[C:21]([CH:18]([CH3:20])[CH3:19])[C:22]([O:34][CH2:35][O:36][CH3:37])=[CH:23][C:24]=3[O:30][CH2:31][O:32][CH3:33])=[CH:11][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 516892Sodium BicarbonateHCID 27960291-Hydroxybenzotriazole hydrateHCID 58236465HCID 58236465, compoundHCID 59829823HCID 59829823, compound

Product 1

HCID 59829844HCID 59829844, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 4-[4-(morpholin-4-yl)-phenyl]semicarbazide (IM9-O-01:70.9 mg, 0.3 mmol) and 5-isopropyl-2,4-bis(methoxymethoxy)-benzoic acid (IM3-a:85.3 mg, 0.3 mmol) in dimethylformamide (4 mL), were added N-methylpyrrolidone (0.2 mL), 1-hydroxybenzotriazole monohydrate (60.8 mg, 0.45 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (115.0 mg, 0.6 mmol) successively, and the mixture was stirred at room temperature overnight. The reaction mixture was mixed with ethyl acetate (30 mL) and 5% aqueous sodium hydrogencarbonate (20 mL). The aqueous layer was separated, and extracted with ethyl acetate. The combined organic layers thus obtained were dried over anhydrous sodium sulfate. Sodium sulfate was removed by filtration, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane: methanol=30:1-20:1) to obtain the title compound (IM5-O-a01: colorless syrup, 104.9 mg, 70%).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate
  3. customThe combined organic layers thus obtained
  4. dry with materialwere dried over anhydrous sodium sulfate
  5. customSodium sulfate was removed by filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (dichloromethane: methanol=30:1-20:1)

Sources & evidence

ORD record
ord-84df0debdbca41b98e5d18f13b96e980
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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