Sodium Iodide → HCID 69916367, compound

HRID 1837278Notes

Reaction equation

HRID 1837278 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][C@@H:22]3[F:27])([CH3:20])[C:18](=[O:28])[CH2:17][CH2:16]4)[C@H:13]([CH2:29][CH2:30][CH2:31][CH2:32]Cl)[CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[Na+].[CH2:36]([NH2:41])[CH2:37][CH2:38][CH2:39][CH3:40]>CN(C)C=O>[CH2:29]([C@@H:13]1[CH2:12][C:11]2[CH:10]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:26]=[CH:25][C:24]=2[C@@H:23]2[C@@H:14]1[C@H:15]1[C@@:19]([CH2:21][C@@H:22]2[F:27])([CH3:20])[C:18](=[O:28])[CH2:17][CH2:16]1)[CH2:30][CH2:31][CH2:32][NH:41][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8060PentylamineHCID 69917378HCID 69917378, compound

Product 1

HCID 69916367HCID 69916367, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 273 mg of 3-benzyloxy-7α-(4-chlorobutyl)-11β-fluor-estra-1,3,5(10)-trien-17-one in 7 ml of dimethylformamide is stirred with 262 mg of sodium iodide and 0.5 ml of n-pentylamine for 24 hours at 80° C. Then, the reaction mixture is added to ice water, extracted with ethyl acetate, washed with saturated sodium chloride solution, dried and concentrated by evaporation in a vacuum. After the crude product is chromatographed on silica gel with a methylene chloride-methanol gradient, 275 mg of 7α-(5-azadecyl)-3-benzyloxy-11β-fluor-estra-1,3,5(10)-trien-17-one is obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. customdried
  4. concentrationconcentrated by evaporation in a vacuum
  5. customAfter the crude product is chromatographed on silica gel with a methylene chloride-methanol gradient

Sources & evidence

ORD record
ord-d1f0b8755a4c4ca1ad91e2da812d0344
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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