Potassium Iodide → HCID 178522742, compound

HRID 255085Notes

Reaction equation

HRID 255085 reaction equation
CS(O[CH2:6][CH2:7][N:8]1[CH:12]=[CH:11][S:10]/[C:9]/1=[N:13]\[C:14]([C:16]12[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2)=[O:15])(=O)=O.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(Cl)Cl>[N:26]1([CH2:6][CH2:7][N:8]2[CH:12]=[CH:11][S:10]/[C:9]/2=[N:13]\[C:14]([C:16]23[CH2:23][CH:22]4[CH2:21][CH:20]([CH2:19][CH:18]([CH2:24]4)[CH2:17]2)[CH2:25]3)=[O:15])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 178505304HCID 178505304, compound

Product 1

HCID 178522742HCID 178522742, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 79A (0.22 g, 0.57 mmol) in 3 mL of acetonitrile was added morpholine (50 μL, 0.63 mmol), potassium iodide (0.11 g, 0.63 mmol), and potassium carbonate (0.17 g, 1.3 mmol). The mixture stirred for 16 hours and then diluted with methylene chloride and was washed with water, saturated aqueous potassium carbonate and brine. The organic phase was dried over anhydrous potassium carbonate, filtered and concentrated tinder reduced pressure. Purification by preparative HPLC afforded 60 mg (28%) of the title compound. 1H NMR (CDCl3, 400 MHz) δ ppm 1.69-1.79 (m, 6 H), 1.96 (d, J=2.8 Hz, 6 H), 2.03 (s, 3 H), 2.48-2.58 (m, 4 H), 2.75 (t, J=6.3 Hz, 2 H), 3.64-3.72 (m, 4 H), 4.28 (t, J=6.3 Hz, 2 H), 6.55 (d, J=4.6 Hz, 1 H), 6.99 (d, J=4.6 Hz, 1 H); MS (DCI/NH3) m/z 376 (M+H)+. Anal. Calculated for C20H29N3O2S: C, 63.97; H, 7.78; N, 11.19. Found: C, 63.85; H, 7.42; N, 10.91.

Workup

  1. washwas washed with water, saturated aqueous potassium carbonate and brine
  2. dry with materialThe organic phase was dried over anhydrous potassium carbonate
  3. filtrationfiltered
  4. concentrationconcentrated tinder reduced pressure
  5. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-90c6d9e8a99541fa8a71cc2c83c9e54a
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Reaction notes

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