Potassium Carbonate → HCID 53627641, compound

HRID 2043178Notes

Reaction equation

HRID 2043178 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH:18]1[N:26]1[CH2:30][CH2:29][NH:28][C:27]1=[O:31].C(=O)([O-])[O-].[K+].[K+]>[Cu]I.CN1C(=O)CCC1>[CH2:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:17][CH:18]1[N:26]1[CH2:30][CH2:29][N:28]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]3[S:13][CH:14]=[CH:15][N:16]=3)(=[O:10])=[O:9])=[CH:4][CH:3]=2)[C:27]1=[O:31]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10193184-Iodo-N-(thiazol-2-yl)benzenesulfonamideHCID 59465644HCID 59465644, compound

Product 1

HCID 53627641HCID 53627641, compoundYield 10.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Synthesized according to general procedure 43. The reaction was set up with 4-iodo-N-(thiazol-2-yl)benzenesulfonamide (250 mg, 0.68 mmol), 1-(2,3-dihydro-1H-inden-2-yl)imidazolidin-2-one (138 mg, 0.68 mmol), copper(I) iodide (267 mg, 1.4 mmol), potassium carbonate (282 mg, 2.0 mmol), and NMP (1.7 mL). The dark mixture was purified via silica gel chromatography using 5% MeOH in CH2Cl2 followed by trituration with 50% Et2O in CH2Cl2 to obtain the desired urea as a white solid (32 mg, 0.07 mmol, 10% yield). 1H NMR (400 MHz, DMSO-d6) δ 12.66 (s, 1H), 7.75-7.69 (m, 4H), 7.26-7.24 (m, 3H), 7.19-7.17 (m, 2H), 6.81 (d, J=4.5 Hz, 1H), 4.74 (dd, J=1.3, 14.2 Hz, 1H), 3.81-3.77 (m, 2H), 3.34-3.27 (m, 2H), 3.12 (dd, J=7.9, 16.1 Hz, 2H), 3.00 (dd, J=6.2, 16.1 Hz, 2H). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=441.2; tR=1.45 min.

Workup

  1. customSynthesized
  2. customThe dark mixture was purified via silica gel chromatography

Sources & evidence

ORD record
ord-93cd134921b44e8390b6cfc9b3cdaeab
Source dataset
uspto-grants-2013_11
Patent number
US08586589B2

Reaction notes

Loading…