Sodium Iodide → HCID 60204455, compound

HRID 2267338Notes

Reaction equation

HRID 2267338 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH3:31])[S:5]([C:8]1[S:9][C:10]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH2:20][CH2:21][N:22]3[C:26]([CH3:28])([CH3:27])[C:25](=[O:29])[NH:24][C:23]3=[O:30])[N:14]=2)=[CH:11][CH:12]=1)(=[O:7])=[O:6].[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1.[I-].[Na+]>CN1CCCC1.[Cl-].[Na+].O>[CH3:27][C:26]1([CH3:28])[N:22]([CH2:21][CH2:20][NH:19][C:15]2[N:14]=[C:13]([C:10]3[S:9][C:8]([S:5]([N:4]([CH3:31])[CH2:3][CH2:2][N:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)(=[O:7])=[O:6])=[CH:12][CH:11]=3)[CH:18]=[CH:17][N:16]=2)[C:23](=[O:30])[NH:24][C:25]1=[O:29]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 31268PyrrolidineHCID 60204410HCID 60204410, compound

Product 1

HCID 60204455HCID 60204455, compound

Reagents, catalysts & solvents 2

HCID 84541-MethylpyrrolidineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of N-(2-chloroethyl)-5-(2-(2-(5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)ethylamino)pyrimidin-4-yl)-N-methylthiophene-2-sulfonamide (200 mg, 0.41 mmol), pyrrolidine (59 mg, 0.82 mmol) and a catalytic amount of sodium iodide in N-methyl-pyrrolidine (5 mL) was heated at 90° C. overnight. After cooling to rt, 50 mL of brine was added and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (3×80 mL), dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuo and the product purified by flash chromatography eluting with methanol (1 M, ammonia)/dichloromethane (1:20) to afford the title compound as a slightly yellow solid (98 mg, 46%). MS (M+H)+ 522.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  2. washThe combined organic layers were washed with brine (3×80 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed in vacuo
  6. customthe product purified by flash chromatography
  7. washeluting with methanol (1 M, ammonia)/dichloromethane (1:20)

Sources & evidence

ORD record
ord-f0b9dd63c1c2497ba840bbe3e8b4bc59
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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