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

HRID 73358Notes

Reaction equation

HRID 73358 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-methoxymethoxybenzoic 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-4d9458c6f3804b2e8223cd638576bf5a
Source dataset
uspto-grants-2014_09
Patent number
US08829040B2

Reaction notes

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