4,7-Dimethoxy-indan-2-ylamine → (R)-8-Benzyloxy-5-[2-(4,7-dimethoxy-indan-2-ylamino)-1-hydroxy-ethyl]-1H-quinolin-2-one

HRID 1815099Notes

Reaction equation

HRID 1815099 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]2[CH2:22][O:21]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]2[C:26]=1[CH2:27][CH:28]([NH2:36])[CH2:29]2>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([OH:21])[CH2:22][NH:36][CH:28]2[CH2:29][C:30]3[C:26](=[C:25]([O:24][CH3:23])[CH:33]=[CH:32][C:31]=3[O:34][CH3:35])[CH2:27]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 112640164,7-Dimethoxy-indan-2-ylamineHCID 114378125-(2R)-2-Oxiranyl-8-(phenylmethoxy)-2(1H)-quinolinone

Product 1

HCID 11386205(R)-8-Benzyloxy-5-[2-(4,7-dimethoxy-indan-2-ylamino)-1-hydroxy-ethyl]-1H-quinolin-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

(R)-8-Benzyloxy-5-oxiranylcarbostyril (100 mg, 0.34 mmol), prepared from literature procedure (Beeley, Lee James; Dean, David Kenneth, PCT Int. Appl. WO 9525104) and 4,7-dimethoxy-indan-2-ylamine (66 mg, 0.34 mmol), prepared from literature procedure (Sindelar, R. D.; Mott, J.; Barfknecht, C. F.; Arneric, S. P.; Flynn, J. R.; Long, J. P.; Bhatnagar, R. K. J. Med. Chem. (1982), 25(7), 858-64), are dissolved in toluene (1 mL). The reaction mixture was heated to 110° C. and the solvent is allowed to evaporate. The residue is then stirred at 110° C. for 4 hours. The reaction is shown to be complete by TLC. The product is purified by flash column chromatography (silica, dichloromethane/methanol 20:1). TLC (silica, dichloromethane/methanol 25:1 Rf=0.10). ES+ MS m/e 487 (MH+).

Workup

  1. customprepared from literature procedure (Sindelar, R. D.; Mott, J.; Barfknecht, C. F.; Arneric, S. P.; Flynn, J. R.; Long, J. P.; Bhatnagar, R. K. J. Med. Chem. (1982), 25(7), 858-64)
  2. customto evaporate
  3. customThe product is purified by flash column chromatography (silica, dichloromethane/methanol 20:1)

Sources & evidence

ORD record
ord-9c9c3662dcaa440088cba5b4712496c8
Source dataset
uspto-grants-2005_04
Patent number
US06878721B1

Reaction notes

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