Tetrabutylammonium Fluoride → HCID 24998851, compound

HRID 1910839Notes

Reaction equation

HRID 1910839 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]([CH2:48][CH2:49][O:50][Si](C)(C)C(C)(C)C)[C:10]1[N:15]=[C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:47])[C:30](=[O:46])[C:31]4[N:39]5[C:34]([CH:35]=[CH:36][CH:37]=[CH:38]5)=[CH:33][C:32]=4[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)[CH:13]=[CH:12][CH:11]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:6][CH2:7][CH2:8][N:9]([CH2:48][CH2:49][OH:50])[C:10]1[N:15]=[C:14]([N:16]2[CH2:17][CH2:18][N:19]([C:22]3[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:47])[C:30](=[O:46])[C:31]4[N:39]5[C:34]([CH:35]=[CH:36][CH:37]=[CH:38]5)=[CH:33][C:32]=4[C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)=[CH:24][CH:23]=3)[CH2:20][CH2:21]2)[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67106966HCID 67106966, compound

Product 1

HCID 24998851HCID 24998851, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-{4-[4-(6-{bis-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-amino}-pyridin-2-yl)-piperazin-1-yl]-phenyl}-2-oxo-2-(2-phenyl-indolizin-3-yl)-acetamide (0.7 g, 0.81 mmol) in THF (10 mL) was added tetra-n-butylammonium fluoride (1.28 g, 4.06 mmol) at 0° C. The reaction mixture was stirred at r.t. for 1 h. The solvent was evaporated in vacuo, the residue diluted with dichloromethane and washed with water, brine, dried over sodium sulfate filtered and concentrated. The crude compound was purified by column chromatography over silica gel (60-120 mesh) using 3% methanol/chloroform to yield N-[4-(4-{6-[bis-(2-hydroxy-ethyl)-amino]-pyridin-2-yl}-piperazin-1-yl)-phenyl]-2-oxo-2-(2-phenyl-indolizin-3-yl)-acetamide (180 mg, 36%) as a light yellow solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionthe residue diluted with dichloromethane
  3. washwashed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude compound was purified by column chromatography over silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-a4b94fd0610b4c1ea850ad8818d0f61d
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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