HCID 22405674, compound → HCID 22405718, compound

HRID 441090Notes

Reaction equation

HRID 441090 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:37])[C:29](=[O:36])[C:30]=5[NH:31][C:32]([CH3:35])([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:37])[C:29](=[O:36])[C:30]=5[NH:31][C:32]([CH3:33])([CH3:34])[CH3:35])[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 22405674HCID 22405674, compound

Product 1

HCID 22405718HCID 22405718, compoundYield 94.2%

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-t-butylamino-3-cyclobuten-3-yl)-1-triisopropylsilylindole (0.294 g, 0.45 mmol) in 10 mL of acetonitrile was added 48% HF (32 μL, 0.90 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 the title compound (0.213 g, 94%) as a yellow foam which could not be crystallized. This material was suspended in excess 1N HCl, a small amount of ethanol was added and the mixture was gently warmed to effect dissolution. Storage of this solution at -20° C. led to crystallization. The crystals were filtered, washed (acetone, ether) and dried in vacuo to give the hydrochloride (0.252 g, 89%) as a light yellow solid, mp 180° C. (softens), 215°-218° C. (foams): IR (KBr) 3400 (br), 1775, 1715, 1635, 1575 (br) cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ 11.58 (br s, 1H), 11.32 (br s, 1H), 8.67 (s, 1H), 8.46 (s, 1H), 8.32 (s, 1H), 8.21 (s, 1H), 7.84 (d, J=8.6 Hz, 1H), 7.49 (d, J=8.4 Hz, 1H), 7.33 (s, 1H), 4.93 (m, 2H), 3.91 (s, 3H), 3.79-3.62 (m, 4H), 3.17 (br s, 4H), 2.84 (t, J=7.0 Hz, 2H), 2.17 (m, 2H), 1.51 (s, 9H). Anal. Calcd for C28H34N6O3. 3 HCl. H2O: C, 53.38; H, 6.24; N, 13.34. Found: C, 53.24; H, 6.35; N, 13.24.

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

Sources & evidence

ORD record
ord-6fda70a84fcd48318766c69306a4a89d
Source dataset
uspto-grants-1996_05
Patent number
US05521188

Reaction notes

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