Sodium Iodide → HCID 58046714, compound

HRID 2362973Notes

Reaction equation

HRID 2362973 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][N:3]1[CH2:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].[Cl:32][C:33]1[CH:34]=[CH:35][C:36]2[NH:40][C:39](=[O:41])[N:38]([CH2:42][CH2:43][CH2:44]Cl)[C:37]=2[CH:46]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Cl:32][C:33]1[CH:34]=[CH:35][C:36]2[NH:40][C:39](=[O:41])[N:38]([CH2:42][CH2:43][CH2:44][N:9]3[CH2:10][CH2:11][C:6]4([N:5]([C:12]5[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=5)[CH2:4][N:3]([CH2:18][C:19]5[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=5)[C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[C:2]4=[O:1])[CH2:7][CH2:8]3)[C:37]=2[CH:46]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 203855876-chloro-1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-oneHCID 58046667Tert-butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Product 1

HCID 58046714HCID 58046714, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
81 °C

Procedure

A mixture of tert-butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (329 mg, 0.7807 mmol, 1 equiv), 6-chloro-1-(3-chloropropyl)-1H-benzo[d]imidazol-2(3H)-one (219 mg, 0.7807 mmol, 1 equiv), sodium iodide (46.81 mg, 0.312 mmol, 0.4 equiv), and potassium carbonate (323.7 mg, 2.34 mmol, 3 equiv) in 2-butanone was stirred at 81° C. for 16 h. After cooling the reaction mixture, the crude mixture was partitioned between ethyl acetate and water. The organic layer was dried over MgSO4, filtered, concentrated, and the crude residue was purified using preparatory thin layer chromatography in 10% methanol in dichloromethane to afford the title compound as a white powder (100 mg, ˜20%); MS for C35H40ClN5O4 m/z 630.15 (M+H)+.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customthe crude mixture was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe crude residue was purified

Sources & evidence

ORD record
ord-7f0bc12e43a14c398ca3a2970965ec26
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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