Toluene → (1-Cyclopentylmethyl-1H-indol-5-yl)-(4-isopropyl-piperazin-1-yl)-methanone

HRID 225437Notes

Reaction equation

HRID 225437 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([N:12]3[CH2:17][CH2:16][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]3)=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:21]1([CH3:27])[CH:26]=[CH:25][CH:24]=[CH:23]C=1>>[CH:24]1([CH2:23][N:1]2[C:9]3[C:4](=[CH:5][C:6]([C:10]([N:12]4[CH2:13][CH2:14][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:16][CH2:17]4)=[O:11])=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH2:25][CH2:26][CH2:21][CH2:27]1

Participants

3

Reactant 2

HCID 1140TolueneHCID 57752818Methanone,1h-indol-5-yl[4-(1-methylethyl)-1-piperazinyl]-2×

Product 1

HCID 25064785(1-Cyclopentylmethyl-1H-indol-5-yl)-(4-isopropyl-piperazin-1-yl)-methanone

Conditions

Temperature
110 °C

Procedure

A mixture of 21.7 mg (0.08 mmol) (1H-indol-5-yl)-(4-isopropyl-piperazin-1-yl)-methanone (intermediate 1), 16 mg (0.16 mmol) cyclopentylmethynol (commercially available), 38.6 mg (0.16 mmol) cyanomethylenetri-n-butylphospborane in toluene was heated to 110° C. for an extended period of time. After evaporation the residue was purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile/water/NEt3. The combined product fractions were evaporated to yield 5.4 mg of the title compound. MS (m/e): 354.4 (MH+).

Workup

  1. customAfter evaporation the residue
  2. customwas purified by preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile/water/NEt3
  5. customThe combined product fractions were evaporated

Sources & evidence

ORD record
ord-8d2014efa3a447e496834ff762e78c46
Source dataset
uspto-grants-2009_07
Patent number
US07557108B2

Reaction notes

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