Potassium Carbonate → HCID 58603139, compound

HRID 1354220Notes

Reaction equation

HRID 1354220 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH:13]1[CH2:15][O:14]1.[C:16]([O:20][C:21]([CH:23]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25][NH:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].Cl([O-])(=O)(=O)=O.[Li+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C(OCC)(=O)C>[C:16]([O:20][C:21]([CH:23]1[CH2:29][CH2:28][N:27]([CH2:15][CH:13]([OH:14])[C:6]2[C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][CH:7]=2)[CH2:26][CH2:25][NH:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11298596HCID 11298596, compoundHCID 15140404tert-Butyl 1,4-diazepane-5-carboxylateHCID 23665649Lithium perchlorate

Product 1

HCID 58603139HCID 58603139, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-methoxy-4-oxiranylquinoline (400 mg, 2 mmol), [1,4]-diazepane-5-carboxylic acid tert-butyl ester (400 mg, 2 mmol, prepared as described in J. Chem. Research (S), 1991, 306, 2876), lithium perchlorate (211 mg, 2 mmol) and potassium carbonate (275 mg, 2 mmol) in DMF (5 ml) was heated at 100° C. for 4 hours. The reaction mixture was diluted with water and ethyl acetate, the aqueous phase was extracted with ethyl acetate and the combined organic phases were dried over sodium sulphate and concentrated. The product was purified by chromatography on silica gel (DCM/MeOH 9:1).

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate
  2. dry with materialthe combined organic phases were dried over sodium sulphate
  3. concentrationconcentrated
  4. customThe product was purified by chromatography on silica gel (DCM/MeOH 9:1)

Sources & evidence

ORD record
ord-0102c04fe1ec4a15b95adfa8a499e9a1
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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