3-Methoxypropanoyl chloride → HCID 22320429, compound

HRID 433200Notes

Reaction equation

HRID 433200 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[C:8]1([S:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=[CH:23][C:22]=2[NH2:31])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>N1C=CC=CC=1>[CH3:1][O:2][CH2:3][CH2:4][C:5]([NH:31][C:22]1[CH:23]=[N:24][C:25]2[C:30]([C:21]=1[NH:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][S:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:6]

Participants

4

Reactant 2

HCID 27597283-Methoxypropanoyl chlorideHCID 86588279HCID 86588279, compound

Product 1

HCID 22320429HCID 22320429, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 3-methoxypropanoyl chloride (2.04 g, 16.6 mmol) in pyridine (20 mL) was slowly added to a chilled (0° C.) solution of N4-[5-(phenylthio)pentyl]quinoline-3,4-diamine (5.1 g, 15.2 mmol) in pyridine. The reaction was allowed to warm to ambient temperature. More acid chloride (1 g) was added and the reaction was heated at reflux overnight. The reaction mixture was concentrated under reduced pressure to provide 6.7 g of 3-methoxy-N-(4-{[5-(phenylthio)pentyl]amino}quinolin-3-yl)propanamide as a sticky brown solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b975e9ab43af40f78ad2f691a3bfa082
Source dataset
uspto-grants-2003_12
Patent number
US06667312B2

Reaction notes

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