Water → HCID 57664590, compound

HRID 1467888Notes

Reaction equation

HRID 1467888 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:9][CH2:10][CH2:11]I)=[CH:4][CH:3]=1.[CH:20]1([N:23]([CH:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)(=[O:26])=[O:25])[CH2:22][CH2:21]1.C([O-])([O-])=O.[K+].[K+].O>C(C(C)=O)C.CCOC(C)=O>[CH:20]1([N:23]([CH:37]2[CH2:42][CH2:41][N:40]([CH2:11][CH2:10][O:9][CH:8]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:39][CH2:38]2)[S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:34])[F:35])[CH:28]=2)(=[O:25])=[O:26])[CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2773944N-Cyclopropyl-N-piperidin-4-yl-3-(trifluoromethyl)benzenesulfonamideHCID 10761917HCID 10761917, compound

Product 1

HCID 57664590HCID 57664590, compound

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

1-[Bis(4-fluorophenyl)-methoxy]-2-iodoethane (36) (294 mg, 0.79 mmol) was dissolved in 5 mL of methyl ethyl ketone and the mixture was added to N-cyclopropyl-N-(4-piperidinyl)-3-(trifluoromethyl)benzenesulfonamide (200 mg, 0.57 mmol) and K2CO3 (157 mg, 1.1 mmol). The mixture was then heated at 80° C. overnight. Water was added to the mixture, and EtOAc was used to extract the product. The organic layer was dried over Na2SO4 and evaporated. The crude product was purified by silica gel column eluting with CH2Cl2 and CH2Cl2/EtOAc (4:1) to afford the title compound 38 as a yellow oil. 1H NMR (CDCl3): δ 8.127 (s, 1H), 8.061-8.042 (d, 1H), 7.856-7.833 (d, 1H), 7.694-7.655 (t, 1H), 7.282-7.233 (m, 4H), 7.035-6.972 (m, 4H), 5.302 (s, 1H), 3.882-3.806 (t, 1H), 3.551-3.491 (t, 2H), 2.965-2.887 (d, 2H), 2.670-2.605 (t, 2H), 2.127-2.064 (t, 2H), 1.986-1.939 (m, 3H), 1.531-1.493 (d, 2H), 0.992-0.952 (m, 2H), 0.794-0.760 (m, 2H). LC: 100%. MS (e/z): 596 (M+H+).

Workup

  1. extractionto extract the product
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated
  4. customThe crude product was purified by silica gel column
  5. washeluting with CH2Cl2 and CH2Cl2/EtOAc (4:1)

Sources & evidence

ORD record
ord-d4dc43f6669f48eba8c2efa1f78a8687
Source dataset
uspto-grants-2015_04
Patent number
US09000174B2

Reaction notes

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