Acetyl chloride → 4-[6-(2-Acetylaminoethyloxy)-3-cyanoindol-1-yl]-2-methoxymethoxybenzoic acid ethyl ester

HRID 1674603Notes

Reaction equation

HRID 1674603 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][CH2:22][NH2:23])[CH:18]=3)[C:13]([C:24]#[N:25])=[CH:12]2)=[CH:7][C:6]=1[O:26][CH2:27][O:28][CH3:29])[CH3:2].C(N(CC)CC)C.[C:38](Cl)(=[O:40])[CH3:39]>ClCCl>[CH2:1]([O:3][C:4](=[O:30])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][CH2:22][NH:23][C:38](=[O:40])[CH3:39])[CH:18]=3)[C:13]([C:24]#[N:25])=[CH:12]2)=[CH:7][C:6]=1[O:26][CH2:27][O:28][CH3:29])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 58437387HCID 58437387, compound

Product 1

HCID 584373154-[6-(2-Acetylaminoethyloxy)-3-cyanoindol-1-yl]-2-methoxymethoxybenzoic acid ethyl esterYield 75.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[6-(2-aminoethyloxy)-3-cyanoindol-1-yl]-2-methoxymethoxy benzoic acid ethyl ester (0.10 g) and triethylamine (0.076 g) in dichloromethane (5 mL) was added acetyl chloride (0.049 g) at room temperature, and this mixture was stirred at room temperature for 12 hours. This reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane:methanol=10:1) to give the title compound (0.083 g).

Workup

  1. concentrationThis reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-889acd2bbab34f789cfea296416bb0de
Source dataset
uspto-grants-2011_08
Patent number
US08003647B2

Reaction notes

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