t-Butylammonium fluoride → (S)-N-[(3-hydroxypropyl)(oxido)phenyl--sulfanylidene]-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide

HRID 607449Notes

Reaction equation

HRID 607449 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][S@:12](=[O:45])([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[N:13][C:14](=[O:38])[C:15]1[CH:20]=[C:19]([C:21]#[C:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][C:30]([C:32]3[O:33][CH:34]=[CH:35][C:36]=3[CH3:37])=[O:31])[CH:24]=2)[CH:18]=[N:17][CH:16]=1)(C(C)(C)C)(C)C.[F-].C([NH3+])(C)(C)C>C1COCC1.CCOC(C)=O>[OH:8][CH2:9][CH2:10][CH2:11][S@:12](=[O:45])([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[N:13][C:14](=[O:38])[C:15]1[CH:20]=[C:19]([C:21]#[C:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][C:30]([C:32]3[O:33][CH:34]=[CH:35][C:36]=3[CH3:37])=[O:31])[CH:24]=2)[CH:18]=[N:17][CH:16]=1

Participants

5

Reactant 2

HCID 21866379t-Butylammonium fluorideHCID 86629484(S)-N-[(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)(oxido)phenyl--sulfanylidene]-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide

Product 1

HCID 86629485(S)-N-[(3-hydroxypropyl)(oxido)phenyl--sulfanylidene]-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of (S)-N-[(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)(oxido)phenyl--sulfanylidene]-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide (2.2 g, 3.43 mmol) in anhydrous THF (60 mL) at 0° C. was added dropwise tert-butylammonium fluoride (7.2 mL, 1 M in THF) and the reaction was stirred at 0° C. for 1 hour. The yellow reaction solution was then concentrated at room temperature to give a red oil. The oily residue was diluted with EtOAc, which was washed with saturated aqueous NaHCO3 (2×), brine (1×), and then dried (anhydrous Na2SO4). The organic layer was decanted, concentrated, and the resulting oily residue was chromatographed (MeOH—CH2Cl2: from 1:100 to 1:50) yielding the title compound as a clear oil which turned into white foam in-vacuo (1.72 g, 95%).

Workup

  1. concentrationThe yellow reaction solution was then concentrated at room temperature
  2. customto give a red oil
  3. washwas washed with saturated aqueous NaHCO3 (2×), brine (1×)
  4. dry with materialdried (anhydrous Na2SO4)
  5. customThe organic layer was decanted
  6. concentrationconcentrated
  7. customthe resulting oily residue was chromatographed (MeOH—CH2Cl2: from 1:100 to 1:50)

Sources & evidence

ORD record
ord-b1dbfeb8230447d086a6c1176ec4e202
Source dataset
uspto-grants-2011_03
Patent number
US07915443B2

Reaction notes

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