Iodoethane → HCID 66580871, compound

HRID 1521859Notes

Reaction equation

HRID 1521859 reaction equation
[N:1]1([C:7]([C:9]2[NH:13][N:12]=[C:11]3[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[S:20](=[O:23])(=[O:22])[CH2:21][C:10]=23)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:30](I)[CH3:31]>C(#N)C>[CH2:30]([N:12]1[C:11]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[S:20](=[O:22])(=[O:23])[CH2:21][C:10]=2[C:9]([C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[O:8])=[N:13]1)[CH3:31]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 52950347HCID 52950347, compound

Product 1

HCID 66580871HCID 66580871, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-(morpholin-4-ylcarbonyl)-2,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxide (0.400 g, 1.2 mmol) in acetonitrile (10 mL) is added potassium carbonate (0.49 g, 3.6 mmol) followed by ethyl iodide (0.56 g, 3.6 mmol). The reaction mixture is heated at 60° C. overnight. The crude reaction mixture is filtered through a celite pad and the filtrate concentrated under reduced pressure. The residue is purified by preparative HPLC to afford the title compound as an off-white solid. 1H NMR (DMSO-d6, 400 MHz): δ 8.02 (d, J=7.72 Hz, 1H), 7.94 (d, J=7.84 Hz, 1H), 7.89 (t, J=7.52 Hz, 1H), 7.72 (t, J=7.64 Hz, 1H), 4.79 (s, 2H), 4.57 (q, J=7.12 Hz, 2H), 3.94 (brs, 2H), 3.66-3.63 (m, 6H), 1.46 (t, J=7.16 Hz, 3H). MS (ESI+): 362.0. HPLC (max plot) 95.0%; Rt 2.99 min.

Workup

  1. customThe crude reaction mixture
  2. filtrationis filtered through a celite pad
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-69105a7db4894d4ab55c78528398d392
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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