Potassium Carbonate → HCID 18438148, compound

HRID 1643186Notes

Reaction equation

HRID 1643186 reaction equation
[CH2:1]([N:5]1[C:9]([CH2:10]O)=[C:8]([F:12])[N:7]=[C:6]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH3:4].S(Cl)(Cl)=O.[CH2:23]([NH2:33])[C:24]1[CH:32]=[CH:31][C:30]2[O:29][CH2:28][O:27][C:26]=2[CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.CN(C=O)C.C(OCC)(=O)C>[O:29]1[C:30]2[CH:31]=[CH:32][C:24]([CH2:23][NH:33][CH2:10][C:9]3[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[N:7][C:8]=3[F:12])=[CH:25][C:26]=2[O:27][CH2:28]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 75799Benzo-1,3-dioxole-5-methylamineHCID 18437786HCID 18437786, compound

Product 1

HCID 18438148HCID 18438148, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Compound 143 (76 mg, 0.30 mmol) is dissolved in 2 ml dichloromethane and cooled to 0° C. Thionyl chloride (0.05 mL) is added and the resulting solution is stirred at room temperature for 2 h. The solvent and excess thionyl chloride are evaporated. The residue is dissolved in 1.0 ml DMF and added to a solution of piperonyl amine (227 mg, 1.5 mmol) in DMF (2 mL) containing 100 mg potassium carbonate. The resulting mixture is stirred at room temperature for 2 h, then diluted with 20 ml of ethyl acetate, washed with water and brine, dried, and concentrated. The resulting residue is purified with silica gel chromatography (hexanes/ethyl acetate, from 2:1 to 1:1) to provide compound 144. MS (+VE) m/z 382 (M+1).

Workup

  1. customThe solvent and excess thionyl chloride are evaporated
  2. dissolutionThe residue is dissolved in 1.0 ml DMF
  3. stirringThe resulting mixture is stirred at room temperature for 2 h
  4. washwashed with water and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe resulting residue is purified with silica gel chromatography (hexanes/ethyl acetate, from 2:1 to 1:1)

Sources & evidence

ORD record
ord-10e38136460548d1b49c1d3088e1a41f
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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