4-Methylmorpholine → HCID 22601457, compound

HRID 2308296Notes

Reaction equation

HRID 2308296 reaction equation
CCN=C=NCCCN(C)C.[NH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][OH:22])=[CH:16][CH:15]=1.[Cl:23][C:24]1[CH:32]=[N:31][CH:30]=[C:29]([Cl:33])[C:25]=1[C:26](O)=[O:27].ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C>[Cl:23][C:24]1[CH:32]=[N:31][CH:30]=[C:29]([Cl:33])[C:25]=1[C:26]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][OH:22])=[CH:16][CH:15]=1)=[O:27]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2×HCID 757711-HydroxybenzotriazoleHCID 6057633,5-Dichloroisonicotinic acidHCID 226014582-[4-(Aminomethyl)phenyl]ethan-1-ol

Product 1

HCID 22601457HCID 22601457, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using the EDCI coupling general procedure F: Reaction of 2-(4-Aminomethyl-phenyl)-ethanol (306 mg, 2.03 mmol), 3,5-dichloroisonicotinic acid (385 mg, 2.03 mmol), 1-hydroxybenzotriazole (301 mg, 2.22 mmol), 4-methyl morpholine (0.50 mL, 4.45 mmol), and EDCI (426 mg, 2.22 mmol) in anhydrous DMF (5 mL) overnight at room temperature and overnight at 40° C. followed by column chromatography on silica gel (2:2:96 MeOH—NH4OH—CH2Cl2) gave the title compound (291 mg, 44%) as a white foam.

Workup

  1. customovernight
  2. customat 40° C.

Sources & evidence

ORD record
ord-11f7e63e707e4c779e2ddde1d434fc07
Source dataset
uspto-grants-2004_12
Patent number
US06835731B2

Reaction notes

Loading…