Sodium Iodide → N-{5-[5-(2,4-Dioxo-1,3,8-triazaspiro[4.5]dec-8-yl)pentanoyl]-2,4-dimethoxyphenyl}-4-(trifluoromethyl)benzenesulfonamide

HRID 1599007Notes

Reaction equation

HRID 1599007 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[C:9]([O:30][CH3:31])=[CH:10][C:11]([O:28][CH3:29])=[C:12]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:13]=1)=[O:7].Cl.[NH:33]1[C:37]2([CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[C:36](=[O:43])[NH:35][C:34]1=[O:44].[I-].[Na+].C(N(CC)CC)C>CN(C=O)C>[O:44]=[C:34]1[NH:35][C:36](=[O:43])[C:37]2([CH2:42][CH2:41][N:40]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]3[C:9]([O:30][CH3:31])=[CH:10][C:11]([O:28][CH3:29])=[C:12]([NH:14][S:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=4)(=[O:17])=[O:16])[CH:13]=3)=[O:7])[CH2:39][CH2:38]2)[NH:33]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 18931280HCID 18931280, compoundHCID 189313001,3,8-Triaza-spiro[4.5]decane-2,4-dione hydrochloride

Product 1

HCID 3693566N-{5-[5-(2,4-Dioxo-1,3,8-triazaspiro[4.5]dec-8-yl)pentanoyl]-2,4-dimethoxyphenyl}-4-(trifluoromethyl)benzenesulfonamideYield 38.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of N-[5-(5-chloropentanoyl)-2,4-dimethoxyphenyl]-4-trifluoromethylbenzenesulfonamide (0.8 g, 1.7 mmol), prepared as in Example 14, 1,3,8-triazaspiro[4.5]decane-2,4-dione hydrochloride (0.55 g, 2.7 mmol), prepared as in Example 16, sodium iodide (0.4 g, 2.7 mmol), triethylamine (0.5 g, 5 mmol) in DMF (approximately 5 mL) was heated 16 hours at 115° C. The mixture was concentrated and the residue was stirred with water and the solids were collected, dried and purified by column chromatography eluting with methylene chloride/methanol+ammonium hydroxide (95:5) to give N-{5-[5-(2,4-dioxo -1,3,8-triazaspiro[4.5]dec-8-yl)pentanoyl]-2,4-dimethoxyphenyl}-4-trifluoromethylbenzenesulfonamide (0.4 g, 0.65 mmol), m.p. 226° C. The free base was recrystallized from a solution of hydrogen chloride in ethanol to give N-{5-[5-(2,4-dioxo-1,3,8-triazaspiro[4.5]dec-8-yl)pentanoyl]-2,4-dimethoxyphenyl}-4-trifluoromethylbenzenesulfonamide hydrochloride (0.37 g, 0.57 mmol), m.p. 277°-278° C. (dec).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe solids were collected
  3. customdried
  4. custompurified by column chromatography
  5. washeluting with methylene chloride/methanol+ammonium hydroxide (95:5)

Sources & evidence

ORD record
ord-31714add8b034205bc04a3236a3d4cb5
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

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