Potassium Iodide → HCID 178522742, compound

HRID 1469969Notes

Reaction equation

HRID 1469969 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 under 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, 6H), 1.96 (d, J=2.8 Hz, 6H), 2.03 (s, 3H), 2.48-2.58 (m, 4H), 2.75 (t, J=6.3 Hz, 2H), 3.64-3.72 (m, 4H), 4.28 (t, J=6.3 Hz, 2H), 6.55 (d, J=4.6 Hz, 1H), 6.99 (d, J=4.6 Hz, 1H); 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 under reduced pressure
  5. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-391601903abd46cda911a2bf7e099018
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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