Bromide ion → HCID 86744993, compound

HRID 2248576Notes

Reaction equation

HRID 2248576 reaction equation
BrCCCC[N:6]1[C:10](=[O:11])[C:9]2([CH2:15][CH2:14][CH2:13][CH2:12]2)[S:8][CH:7]1[CH3:16].[N:17]1([C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH:25][N:24]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[Br-]>C(OCC)(=O)C.C(#N)C>[NH:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]([N:17]2[CH2:22][CH2:21][N:20]([CH2:10][CH2:9][CH2:12][CH2:13][C:7]3([CH3:16])[NH:6][C:10](=[O:11])[C:9]4([CH2:12][CH2:13][CH2:14][CH2:15]4)[S:8]3)[CH2:19][CH2:18]2)=[N:24]1

Participants

8

Reactant 5

HCID 259Bromide ionHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 107809503-(4-Bromobutyl)-2-methyl-1-thia-3-azaspiro[4.4]nonan-4-oneHCID 148234453-(Piperazin-1-YL)-1H-indazole

Product 1

HCID 86744993HCID 86744993, compoundYield 171.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(4-bromobutyl)-2-methyl-1-thia-3-azaspiro[4.4]nonan-4-one (4.20 g), 3-(1-piperazinyl)-1H-indazole (3.0 g), K2CO3 (5.68 g), NaI (310 mg), and acetonitrile (220 ml) was heated between 60° and 80° C. under nitrogen. After 18 hours, TLC analysis showed only a trace of the starting bromide. The mixture was cooled to ambient temperature, ethyl acetate (150 ml) was added, the inorganics filtered, and the filtrate concentrated under reduced pressure. The residue was taken up in dichloromethane (230 ml), washed with H2O (130 ml), brine (130 ml), dried (Na2SO4), and concentrated to a foam. The foam was chromatographed on silica gel, diluting with 8% methanol in dichloromethane, to furnish 5.04 g of a foam which solidified upon addition of ether/hexanes. The solid was recrystallized from ethyl acetate/hexanes to give 3.72 g of 3-(4-(1-[1 H-indazol-3-yl]-4-piperazinyl)butyl)-2-methyl-1-thia-3-azaspiro[4.4]non-4-one, m.p. 113°-115° C.

Workup

  1. temperaturewas heated between 60° and 80° C. under nitrogen
  2. filtrationthe inorganics filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. washwashed with H2O (130 ml), brine (130 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to a foam
  7. customThe foam was chromatographed on silica gel
  8. additiondiluting with 8% methanol in dichloromethane

Sources & evidence

ORD record
ord-5853e486cb6443c1909c6eb0d9b1f17c
Source dataset
uspto-grants-1991_08
Patent number
US05041445

Reaction notes

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