Bromide ion → HCID 10501072, compound

HRID 2392793Notes

Reaction equation

HRID 2392793 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=O)[CH2:9][S:8][CH2:7]1.[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[C:14]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[N:13]=1.[C:28]([O-:31])([O-])=O.[K+].[K+].[Na+].[I-].[Br-].CO.[CH2:39](Cl)Cl>CCOC(C)=O.CCCCCC.C(#N)C>[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[C:14]([N:22]2[CH2:23][CH2:24][N:25]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:28](=[O:31])[C:9]([CH3:10])([CH3:39])[S:8][CH2:7]3)[CH2:26][CH2:27]2)[N:13]=1

Participants

9

Reactant 6

HCID 259Bromide ionHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 108475053-(4-Bromobutyl)-4-thiazolidinoneHCID 130255693-(Piperazin-1-yl)isoquinolineHCID 21226129Dichloromethane methanol

Product 1

HCID 10501072HCID 10501072, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 3-(4-bromobutyl)-4-thiazolidinone (4.00 g), 1-(3-isoquinolinyl)piperazine (3.53 g), K2CO3 (6.22 g), NaI (300 mg) and acetonitrile (190 mL) was heated at 75° C. (bath temperature) under N2. After 16 h, TLC analysis (silica gel, 40% EtOAc/hexane) showed the absence of starting bromide and a major product at Rf =0.22 (silica gel, 5% MeOH/CH2Cl2). The reaction mixture was cooled to ambient temperature and filtered, the inorganic solid was washed with hot ethyl acetate, and the wash was combined with the above filtrate and concentrated in vacuo to a green solid. The solid was triturated with hot ethyl acetate (300 mL) and the mixture filtered. The filtrate was concentrated in vacuo to a solid which was chromatographed (Waters Prep 500, 1 silica gel column, 5% MeOH/CH2 Cl2) to yield 5.10 g of a green solid. The solid was recrystallized from methylene chloride/hexanes to give 2.99 g of light green crystals, mp 145°-146.5° C.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. washthe inorganic solid was washed with hot ethyl acetate
  4. concentrationconcentrated in vacuo to a green solid
  5. customThe solid was triturated with hot ethyl acetate (300 mL)
  6. filtrationthe mixture filtered
  7. concentrationThe filtrate was concentrated in vacuo to a solid which
  8. customwas chromatographed (Waters Prep 500, 1 silica gel column, 5% MeOH/CH2 Cl2)

Sources & evidence

ORD record
ord-6d4053f44dd4485d8b6a27c11cb0272a
Source dataset
uspto-grants-1998_09
Patent number
US05801186

Reaction notes

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