Water → HCID 67444919, compound

HRID 1396160Notes

Reaction equation

HRID 1396160 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Cl:19])[CH:18]=[C:13]3[C:12]([CH2:20][C:21]3[CH:22]=[N:23][C:24]([NH:27][CH:28]4[CH2:33][CH2:32][CH:31]([CH3:34])[CH2:30][CH2:29]4)=[N:25][CH:26]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[Cl:19][C:17]1[CH:18]=[C:13]2[C:12]([CH2:20][C:21]3[CH:22]=[N:23][C:24]([NH:27][CH:28]4[CH2:33][CH2:32][CH:31]([CH3:34])[CH2:30][CH2:29]4)=[N:25][CH:26]=3)=[CH:11][NH:10][C:14]2=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 67444576HCID 67444576, compound

Product 1

HCID 67444919HCID 67444919, compoundYield 1.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To [5-(1-benzenesulfonyl-5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyrimidin-2-yl]-(4-methyl-cyclohexyl)-amine (64, 0.120 g, 0.242 mmol) in 5.0 mL of tetrahydrofuran, tetrabutylammonium fluoride trihydrate (0.20 g, 0.63 mmol) is added. The reaction is stirred at room temperature overnight, then poured into water and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with 20-100% ethyl acetate in hexane. Appropriate fractions are collected and concentrated under vacuum to provide the desired compound (P-3009, 1.4 mg). MS (ESI) [M+H+]+=355.95.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting material is purified by silica gel column chromatography
  6. washeluting with 20-100% ethyl acetate in hexane
  7. customAppropriate fractions are collected
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1bf5d2e833bb4ab982832157f72d356c
Source dataset
uspto-grants-2014_12
Patent number
US08901118B2

Reaction notes

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