Sodium Iodide → HCID 58046706, compound

HRID 2362953Notes

Reaction equation

HRID 2362953 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[CH2:33][CH2:34][CH2:35][CH:36]([C:44]1[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=1)[C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(=O)CC>[F:43][C:40]1[CH:39]=[CH:38][C:37]([CH:36]([C:44]2[CH:45]=[CH:46][C:47]([F:50])=[CH:48][CH:49]=2)[CH2:35][CH2:34][CH2:33][N:9]2[CH2:10][CH2:11][C:6]3([N:5]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:4][N:3]([CH2:18][C:19]4[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=4)[C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[C:2]3=[O:1])[CH2:7][CH2:8]2)=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 58046667Tert-butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Product 1

HCID 58046706HCID 58046706, compoundYield 80.8%

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 (400 mg, 0.949 mmol, 1 equiv), 4,4′-(4-chlorobutane-1,1-diyl)bis(fluorobenzene) (222.06 μl, 0.949 mmol, 1 equiv), potassium carbonate (393.5 mg, 2.847 mmol, 3 equiv), and sodium iodide (42.7 mg, 0.285 mmol, 0.3 equiv) in 2-butanone was stirred at 81° C. for 16 h. After cooling, the reaction mixture was filtered, filtrate concentrated, and the crude residue was purified using the Biotage flash chromatography system (SNAP 50 g cartridge, Rf=0.5, gradient—1%-10% methanol in dichloromethane) to afford the title compound as a white crystalline solid (500 mg, 80.8%); 1H NMR (400 MHz, DMSO-d6): δ 1.35 (bs, 2H); 1.51 (s, 9H); 1.59 (d, 2H, J=13.2 Hz); 2.02-2.04 (m, 2H); 2.36 (bs, 2H); 2.52-2.53 (m, 2H); 2.64-2.67 (m, 4H); 4.11 (s, 1H); 4.57 (s, 2H); 4.60 (s, 2H); 6.75 (bs, 1H); 6.81 (d, 2H, J=8.4 Hz); 7.08-7.12 (m, 4H); 7.16-7.20 (m, 2H); 7.32-7.36 (m, 4H); 7.49-7.53 (m, 2H); 7.78 (bs, 1H); 7.82-7.84 (m, 1H); MS for C4iH45F2N3O3 m/z 666.18 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. concentrationfiltrate concentrated
  4. customthe crude residue was purified

Sources & evidence

ORD record
ord-320b7a3f268e43878b58a2c5880c775a
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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