Dimethylformamide → HCID 19363510, compound

HRID 850514Notes

Reaction equation

HRID 850514 reaction equation
[NH2:1][C:2]1[C:18]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=[CH:15][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)=[O:5].[CH3:27]OC(OC)N(C)C.CN(C=O)C.C(=O)([O-])O.[Na+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>[CH3:26][O:25][C:17]1[C:18]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:2]2[C:3]([C:4](=[O:5])[N:6]([CH2:7][CH2:8][C:9]3[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=3)[CH:27]=[N:1]2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 516892Sodium BicarbonateHCID 19363469HCID 19363469, compound

Product 1

HCID 19363510HCID 19363510, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

2-Amino-4-methoxy-3-pentyloxy-N-(2-pyridin-4-ylethyl)benzamide (100 mg, 0.280 mmol) obtained in Example 2-61, dimethyl formamide dimethyl acetal (0.19 ml, 1.4 mmol) and DMF (0.5 ml) were mixed, and p-toluene sulfonate monohydrate (2 mg, 0.011 mmol) was added to this solution. The mixture was stirred at 130° C. for 5 hours, and ethyl acetate (15 ml) and saturated aqueous sodium hydrogencarbonate solution (15 ml) were added to separate the organic layer. The organic layer was washed with saturated bnne (15 ml), and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (chloroform/methanol=25/1) to give 7-methoxy-8-pentyloxy-3-(2-pyridin-4-ylethyl)-3H-quinazolin-4-one (57 mg, 55%) as a pale-yellow oil.

Workup

  1. customto separate the organic layer
  2. washThe organic layer was washed with saturated bnne (15 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by column chromatography on silica gel (chloroform/methanol=25/1)

Sources & evidence

ORD record
ord-29ee2d2146b44cb4991e02df11bf31c5
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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