Sodium Iodide → HCID 19921628, compound

HRID 1463352Notes

Reaction equation

HRID 1463352 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][S:19]([N:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[CH:16]=2)[NH:11][CH:10]=1)(=O)=O.[I-].[Na+].C(N(CC)C(C)C)(C)C.[CH3:36][O:37][C:38]1[C:39]([N:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)=[N:40][CH:41]=[N:42][CH:43]=1>C(#N)C>[CH3:23][N:22]([CH3:24])[S:19]([CH2:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH2:8][CH2:7][CH2:6][N:47]1[CH2:48][CH2:49][N:44]([C:39]2[C:38]([O:37][CH3:36])=[CH:43][N:42]=[CH:41][N:40]=2)[CH2:45][CH2:46]1)(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 104201525-Methoxy-4-(piperazin-1-yl)pyrimidineHCID 19921694HCID 19921694, compound

Product 1

HCID 19921628HCID 19921628, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of crude 3-[5-[[(dimethylamino)sulfonyl]methyl]-1H-indol-3-yl]propyl methanesulfonate (1.4 mmol, 1.0 equiv.) in 10 mL of anhydrous acetonitrile was added 0.225 g (1.50 mmol, 1.1 equiv.) of sodium iodide, 0.26 mL (1.50 mmol, 1.1 equiv.) of N,N-diisopropylethylamine and 0.291 g (1.50 mmol, 1.1 equiv.) of 1-(5-methoxy-4-pyrimidinyl)piperazine. The mixture was heated to reflux for sixteen hours. The reaction mixture was concentrated in vacuo and the residue was taken up in 50 mL of ethyl acetate. The organic layer was washed with a 10 mL portion of 10% potassium carbonate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield an oil. The oil was purified by chromatography on silica gel using 5% methanol in methylene chloride containing 0.5% concentrated aqueous ammonium hydroxide to obtain 0.403 g (62%) of 1-[3-[5-[[(dimethylamino)sulfonyl]-methyl]-1H-indol-3-yl]propyl]-4-(5-methoxy-4- pyrimidinyl)piperazine. The hydrochloride salt was prepared by addition of 3N ethanolic HCl. Two recrystallizations from methanol gave 0.323 g (64%) of 1-[3-[ 5-[[(dimethyl-amino)sulfonyl]methyl]-1H-indol-3-yl]propyl]-4-(5-methoxy-4-pyrimidinyl)piperazine hydrochloride hydrate, m.p. 210° C. (d). Elemental analysis calculated for C23H32N6O3S/3 HCl/0.5 H2O: C, 46.74; H, 6.14; N, 14.22; found: C., 46.82; H, 6.42; N, 14.09.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for sixteen hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. washThe organic layer was washed with a 10 mL portion of 10% potassium carbonate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto yield an oil
  9. customThe oil was purified by chromatography on silica gel using 5% methanol in methylene chloride containing 0.5% concentrated aqueous ammonium hydroxide

Sources & evidence

ORD record
ord-f01d744af1794afeb9986be594f4c769
Source dataset
uspto-grants-1994_04
Patent number
US05300506

Reaction notes

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