Potassium Carbonate → HCID 71513875, compound

HRID 588754Notes

Reaction equation

HRID 588754 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][C:13]([NH2:23])=[N:14][C:15]=3[N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[S:10][N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:30][C:31]1[CH:41]=[CH:40][C:34]([O:35][CH2:36][C:37](Cl)=[O:38])=[CH:33][CH:32]=1>O1CCOCC1>[NH2:23][C:13]1[N:12]=[C:11]2[S:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:16]2=[C:15]([N:17]2[CH2:18][CH2:19][N:20]([C:37](=[O:38])[CH2:36][O:35][C:34]3[CH:40]=[CH:41][C:31]([Cl:30])=[CH:32][CH:33]=3)[CH2:21][CH2:22]2)[N:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77771p-Chlorophenoxyacetyl chlorideHCID 117642421HCID 117642421, compound

Product 1

HCID 71513875HCID 71513875, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of Example 15 (0.2 mmol) and potassium carbonate (0.2 mmol) in 1,4-dioxane (5 mL) was added 4-chlorophenoxyacetyl chloride (0.2 mmol). The reaction mixture was stirred at room temperature for 1 hour. After concentration under reduced pressure, the crude residue was purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio of 1:60), yielding the pure title compound (80 mg, 80%) as a yellowish solid. MS (m/z) 499.2 [M+H]+ (100%). 1H NMR δH (300 MHz, DMSO-d6, 25° C.) 7.72 (dd, J 8.4, 5.6 Hz, 2H), 7.38 (t, J 8.7 Hz, 2H), 7.30 (d, J 8.8 Hz, 2H), 7.08 (s, 2H, NH2), 6.89 (d, J 8.8 Hz, 2H), 4.76 (s, 2H), 3.34 (br s, 4H), 3.20 (br s, 4H).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe crude residue was purified by flash chromatography on silica
  3. additiona mixture of methanol and dichloromethane (in a ratio of 1:60),

Sources & evidence

ORD record
ord-0ab51a657f5b49ab8ab9c4cc36aaec92
Source dataset
uspto-grants-2016_01
Patent number
US09227984B2

Reaction notes

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