HCID 59588790, compound → HCID 23728853, compound

HRID 1944667Notes

Reaction equation

HRID 1944667 reaction equation
Br[C:2]1[CH:21]=[CH:20][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][N:12]([CH:15]4[CH2:19][CH2:18][CH2:17][CH2:16]4)[CH2:11][CH2:10]3)[S:8][C:4]=2[CH:3]=1.[Cu][C:23]#[N:24]>CN1CCCC1=O.[Cu]I>[CH:15]1([N:12]2[CH2:13][CH2:14][N:9]([C:7]3[S:8][C:4]4[CH:3]=[C:2]([C:23]#[N:24])[CH:21]=[CH:20][C:5]=4[N:6]=3)[CH2:10][CH2:11]2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 59588790HCID 59588790, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 23728853HCID 23728853, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 6-bromo-2-(4-cyclopentylpiperazin-1-yl)benzothiazole (0.54 g, 1.50 mmol) in N-methylpyrrolidin-2-one (100 mL) was added copper(I)iodide (344 mg, 1.80 mmol) and copper(I)cyanide (270 mg, 3.0 mmol). The mixture was heated at 160° C. for 4 h, then allowed to cool to room temperature and filtered. The filtercake was washed with ethyl acetate and the filtrate was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by preparative HPLC to afford 140 mg (30%) of 2-(4-cyclopentylpiperazin-1-yl)benzothiazole-6-carbonitrile.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. washThe filtercake was washed with ethyl acetate
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-1b2341fe9c1a4832b9e750dbd2e4cc89
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

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