HCID 22405669, compound → HCID 22405705, compound

HRID 441089Notes

Reaction equation

HRID 441089 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:27]5[C:28](=[O:36])[C:29](=[O:35])[C:30]=5[NH:31][CH:32]([CH3:34])[CH3:33])[CH:25]=4)[N:20]([Si](C(C)C)(C(C)C)C(C)C)[CH:19]=3)[CH2:11][CH2:10]2)=[N:5][CH:6]=[N:7][CH:8]=1>C(#N)C>[CH3:1][O:2][C:3]1[C:4]([N:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:27]5[C:28](=[O:36])[C:29](=[O:35])[C:30]=5[NH:31][CH:32]([CH3:33])[CH3:34])[CH:25]=4)[NH:20][CH:19]=3)[CH2:13][CH2:14]2)=[N:5][CH:6]=[N:7][CH:8]=1

Participants

3

Reactant 1

HCID 22405669HCID 22405669, compound

Product 1

HCID 22405705HCID 22405705, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-[3-[4-(5-methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-(1,2-dioxo-4-isopropylamino-3-cyclobuten-3-yl) -1-triisopropylsilylindole (0.270 g, 0.42 mmol) in 10 mL of acetonitrile was added 48% HF (30 μL, 0.84 mmol) and the mixture was stirred at room temperature for 2 h. The resulting mixture was evaporated and the residue was partitioned between saturated aqueous NaHCO3 and ethyl acetate. The organic phase was separated and the aqueous phase was back-extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4) and evaporated to give a yellow foam. Crystallization from ethanol at -20° C. afforded the title compound (0.192 g, 94%) as a light yellow solid, mp 104°-106° C.: IR (KBr) 3230 (br), 1768, 1710, 1580 (br) cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ11.15 (s, 1H), 8.77 (d, J=8.6 Hz, 1H), 8.35 (s, 1H), 8.22 (s, 1H), 8.01 (s, 1H), 7.75 (d, J=8.5 Hz, 1H), 7.46 (d, J=8.5 Hz, 1H), 7.25 (d, J=1.7 Hz, 1H), 4.59 (m, 1H), 4.35 (t, J=5.1 Hz, 2H), 3.82 (s, 3H), 3.68 (br s, 4H), 3.43 (m, 1.7H, CH3CH2OH), 2.78 (t, J=7.4 Hz, 2H), 2.5-2.3 (m, 6H), 1.86 (m, 2H), 1.31 (d, J=6.5 Hz, 6H), 1.05 (t, J=7.0 Hz, 2.6H, CH3CH2OH). Anal. Calcd for C24H26N6O3. 0.5 H2O. 0.85 C2H6O: C, 64.22; H, 7.15; N, 15.66. Found: C, 64.30; H, 6.78; N, 15.48.

Workup

  1. customThe resulting mixture was evaporated
  2. customthe residue was partitioned between saturated aqueous NaHCO3 and ethyl acetate
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was back-extracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. customevaporated
  7. customto give a yellow foam
  8. customCrystallization from ethanol at -20° C.

Sources & evidence

ORD record
ord-1c7c7fb8975747e0a5a996e73cf193bb
Source dataset
uspto-grants-1996_05
Patent number
US05521188

Reaction notes

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