Propionyl chloride → HCID 89932753, compound

HRID 1775449Notes

Reaction equation

HRID 1775449 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[NH:7][C:6]=1[C:16]([NH:18][CH3:19])=[O:17].C(N(C(C)C)CC)(C)C.[C:29](Cl)(=[O:32])[CH2:30][CH3:31]>ClCCl>[CH3:15][O:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:16]([NH:18][CH3:19])=[O:17])=[C:5]2[CH2:4][CH2:3][NH:2][C:29](=[O:32])[CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 118071469HCID 118071469, compound

Product 1

HCID 89932753HCID 89932753, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-(2-aminoethyl)-5-methoxy-N-methyl-1H-indole-2-carboxamide hydrochloride (80.0 mg) and dichloromethane (4.44 mL) were added diisopropylethylamine (0.145 mL) and propionyl chloride (0.0296 mL), followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=10:0 to 10:1). The obtained residue was solidified with a mixed solvent of hexane:ethyl acetate=2:1 to obtain 5-methoxy-N-methyl-3-[2-(propionylamino)ethyl]-1H-indole-2-carboxamide (56.0 mg) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (chloroform:methanol=10:0 to 10:1)

Sources & evidence

ORD record
ord-1cab46db7e824f79b867eb6411dbcef8
Source dataset
uspto-grants-2016_02
Patent number
US09260445B2

Reaction notes

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