3-Methoxybenzoic Acid → HCID 67256308, compound

HRID 1847209Notes

Reaction equation

HRID 1847209 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH2:10][CH2:11][NH2:12])=[CH:2]1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18](O)=[O:19].ON1C2N=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>O1CCCC1.CN(C)C=O>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([NH:12][CH2:11][CH2:10][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:1][CH:2]=1)=[O:19]

Participants

8

Reactant 5

HCID 114613-Methoxybenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 54881977-Azatryptamine

Product 1

HCID 67256308HCID 67256308, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of [2-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl]amine (580 mg) and 3-methoxybenzoic acid (658 mg) in tetrahydrofuran (5 mL) and N,N-dimethylformamide (3 mL), 1-hydroxy-7-azabenzotriazole (HOAt) (588 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) hydrochloride (826 mg) were added, followed by stirring at room temperature until materials disappear. To the reaction mixture, ice water and an aqueous saturated sodium hydrogen carbonate solution were sequentially added and then extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:8) to obtain the titled compound having the following physical properties (612 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:8)

Sources & evidence

ORD record
ord-7b60da65e5554e8093bd596ba50fc9d6
Source dataset
uspto-grants-2015_02
Patent number
US08952158B2

Reaction notes

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