Tetrabutylammonium Fluoride → HCID 59743597, compound

HRID 1947050Notes

Reaction equation

HRID 1947050 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]([S:41]([CH3:44])(=[O:43])=[O:42])[CH:10]1[CH2:15][CH2:14][CH:13]([NH:16][C:17]2[N:22]=[C:21]([N:23]3[C:31]4[C:26](=[C:27]([N:32]5[CH2:37][CH2:36][N:35]([C:38](=[O:40])[CH3:39])[CH2:34][CH2:33]5)[CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24]3)[CH:20]=[CH:19][N:18]=2)[CH2:12][CH2:11]1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[C:38]([N:35]1[CH2:36][CH2:37][N:32]([C:27]2[CH:28]=[CH:29][CH:30]=[C:31]3[C:26]=2[CH:25]=[CH:24][N:23]3[C:21]2[CH:20]=[CH:19][N:18]=[C:17]([NH:16][CH:13]3[CH2:12][CH2:11][CH:10]([N:9]([CH2:8][CH2:7][OH:6])[S:41]([CH3:44])(=[O:43])=[O:42])[CH2:15][CH2:14]3)[N:22]=2)[CH2:33][CH2:34]1)(=[O:40])[CH3:39]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69309814HCID 69309814, compound

Product 1

HCID 59743597HCID 59743597, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-{1-[2-(4-{[2-(t-Butyl-dimethyl-silanyloxy)-ethyl]-methanesulfonylamino}-cyclo-hexylamino)-pyrimidin-4-yl]-1H-indol-4-yl}-4-acetyl-piperazine (0.119 g, 0.178 mmol) in THF (2.5 mL) was cooled in an ice bath under N2, and TBAF (0.18 mL, 1.01 eq) slowly added. The reaction mixture was allowed to warm to RT slowly, and stirred at RT for 15 h. The product was taken up in water and EtOAc, extracted with EtOAc, and the organic fractions washed with water, dried over Na2SO4, concentrated, and chromatographed (0% to 5% MeOH/DCM) to provide N-(4-{4-[4-(4-acetyl-piperazin-1-yl)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-N-(2-hydroxy-ethyl)-methanesulfonamide (Compound 320, 61.4 mg, 62%).

Workup

  1. extractionEtOAc, extracted with EtOAc
  2. washthe organic fractions washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customchromatographed (0% to 5% MeOH/DCM)

Sources & evidence

ORD record
ord-7346f83b1d324b83a756d4cbf166e8ae
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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