1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69103424, compound

HRID 2217238Notes

Reaction equation

HRID 2217238 reaction equation
[NH2:1][C:2]1[C:3]([C:24]([OH:26])=O)=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:21]([CH3:23])[CH3:22])[CH:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.Cl.CN.[CH2:30]([N:32]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.CCOC(C)=O.O>[NH2:1][C:2]1[C:3]([C:24]([NH:32][CH3:30])=[O:26])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:21]([CH3:23])[CH3:22])[CH:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6364545Methylamine hydrochlorideHCID 69103454HCID 69103454, compound

Product 1

HCID 69103424HCID 69103424, compoundYield 55.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridyl)-5-phenyl-2-pyrazinecarboxylic acid (70 mg), methylamine hydrochloride (14.8 mg), 1-ethyl-3-[3′-(dimethylamino)propyl]-carbodiimide (34.1 mg), and 1-hydroxy-benzotriazole (29.7 mg) in CH2Cl2 (0.7 ml) was stirred at 25° C. for 4 hours. Water and EtOAc were poured into the mixture. The organic layer was separated, washed with water, sat. aq. NaHCO3, and brine, and dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by silica-gel column chromatography (n-hexane-EtOAc then CH2Cl2—MeOH) and then crystallized from MeOH-IPE to give 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridyl)-N-methyl-5-phenyl-2-pyrazinecarboxamide (40 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with water, sat. aq. NaHCO3, and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by silica-gel column chromatography (n-hexane-EtOAc
  6. customCH2Cl2—MeOH) and then crystallized from MeOH-IPE

Sources & evidence

ORD record
ord-e4f12187ad64495cb7d568aeeab16013
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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