2,3-Dihydroxybutanedioic Acid → 7-benzyloxy-5-{1-hydroxy-2-[2-(4-methoxy-phenyl)-1,1-dimethyl-ethylamino]-ethyl}-1H-quinolin-2-one

HRID 969466Notes

Reaction equation

HRID 969466 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:19])[NH:16]2)=[C:11]([CH:20]2[CH2:22][O:21]2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]([NH2:35])([CH3:34])[CH3:33])=[CH:27][CH:26]=1.C(O)(C)C.C(O)(=O)C(C(C(O)=O)O)O>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:19])[NH:16]2)=[C:11]([CH:20]([OH:21])[CH2:22][NH:35][C:32]([CH3:34])([CH3:33])[CH2:31][C:28]2[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8752,3-Dihydroxybutanedioic AcidHCID 3776IsopropanolHCID 918922-(4-Methoxyphenyl)-1,1-dimethylethylamineHCID 574693717-benzyloxy-5-oxiranyl-1H-quinolin-2-one

Product 1

HCID 694624247-benzyloxy-5-{1-hydroxy-2-[2-(4-methoxy-phenyl)-1,1-dimethyl-ethylamino]-ethyl}-1H-quinolin-2-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

150 mg (0.51 mmol) 7-benzyloxy-5-oxiranyl-1H-quinolin-2-one and 208 mg (1.2 mmol) 2-(4-methoxy-phenyl)-1,1-dimethyl-ethylamine are combined with 1 mL isopropanol and irradiated with microwaves for a total of 1 hour at 135° C. Then the reaction mixture is combined with ethyl acetate and 0.5 molar tartaric acid, whereupon a precipitate is formed. The organic phase is discarded and the solid and the aqueous phase are extracted with dichloromethane/methanol. The combined organic phases are evaporated down and combined with 8 mL ethyl acetate. The insoluble solid is suction filtered and dried. Yield: 130 mg (54%).

Workup

  1. customirradiated with microwaves for a total of 1 hour at 135° C
  2. customis formed
  3. extractionthe solid and the aqueous phase are extracted with dichloromethane/methanol
  4. customThe combined organic phases are evaporated down
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-0f6065f73f3749c3998855184b6a511f
Source dataset
uspto-grants-2007_12
Patent number
US07307076B2

Reaction notes

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