1-Propanol → HCID 10404867, compound

HRID 2111628Notes

Reaction equation

HRID 2111628 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[C:7](=[O:12])[N:6]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH:5]2[CH2:19][C:20]([OH:22])=[O:21].[CH2:23](O)[CH2:24][CH3:25].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[C:7](=[O:12])[N:6]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH:5]2[CH2:19][C:20]([O:22][CH2:23][CH2:24][CH3:25])=[O:21]

Participants

6

Reactant 3

HCID 10311-PropanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23084542HCID 23084542, compound

Product 1

HCID 10404867HCID 10404867, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5,6-dimethyl-3-carboxymethyl-2-(3-pyridyl)isoindolin-1-one [IUPAC name: 2-[5,6-dimethyl-3-oxo-2-(3-pyridinyl)-2,3-dihydro-1H-isoindol-1-yl]acetic acid] (74 mg, 0.25 mmol), n-propyl alcohol (16 mg, 0.27 mmol) and 4-dimethylaminopyridine (3 mg, 0.025 mmol) in dichloromethane was added 1-ethyl-3-(3-dimethylamino-propyl)carbodiimide hydrochloride (53 mg, 0.27 mmol) at 5° C. and the temperature was raised to 25° C. over a period of 1.5 hrs. The reaction solution was concentrated under reduced pressure, and water was added to the residue, followed by extracting with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, successively water, dried, and concentrated under reduced pressure to give 34 mg of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionby extracting with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, successively water
  5. customdried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2d226c0ed420444d8eb791ce47e90702
Source dataset
uspto-grants-2009_04
Patent number
US07521451B2

Reaction notes

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