1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59287375, compound

HRID 1927223Notes

Reaction equation

HRID 1927223 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([CH2:11][O:12][CH3:13])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].CC[N:16]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl-].[NH4+].C(N(C(C)C)CC)(C)C>O.CS(C)=O>[NH2:1][C:2]1[N:10]=[C:9]([CH2:11][O:12][CH3:13])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:16])=[O:5]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 231304372-Amino-6-methoxymethylnicotinic acid

Product 1

HCID 59287375HCID 59287375, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

2-Amino-6-methoxymethyl-nicotinic acid (0.50 g), WSC (1.1 g), HOBt (0.74 g), ammonium chloride (0.44 g), diisopropylethylamine (2.6 g), and DMSO (10 mL) were stirred for 29 hours at room temperature. Water was added thereto, and then the reaction solution was extracted with ethyl acetate. The organic layer was concentrated and purified by NH silica gel column chromatography (ethyl acetate). Ethyl acetate was added to the residue thus obtained, and the solids were filtered off to obtain the titled compound (290 mg).

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. custompurified by NH silica gel column chromatography (ethyl acetate)
  4. additionEthyl acetate was added to the residue
  5. customthus obtained
  6. filtrationthe solids were filtered off

Sources & evidence

ORD record
ord-ffbb4e3732254ac0a69bc17904f0a7bb
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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