Tetrabutylammonium Fluoride → 5-Ethynyl-2-{[6-(morpholin-4-ylmethyl)pyridin-2-yl]amino}thiophene-3-carboxamide

HRID 386141Notes

Reaction equation

HRID 386141 reaction equation
[Si]([C:8]#[C:9][C:10]1[S:14][C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[N:17]=2)=[C:12]([C:29]([NH2:31])=[O:30])[CH:11]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[C:9]([C:10]1[S:14][C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[N:17]=2)=[C:12]([C:29]([NH2:31])=[O:30])[CH:11]=1)#[CH:8]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 595262105-{[tert-Butyl(dimethyl)silyl]ethynyl}-2-{[6-(morpholin-4-ylmethyl)pyridin-2-yl]amino}thiophene-3-carboxamide

Product 1

HCID 595262705-Ethynyl-2-{[6-(morpholin-4-ylmethyl)pyridin-2-yl]amino}thiophene-3-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-{[tert-butyl(dimethyl)silyl]ethynyl}-2-{[6-(morpholin-4-ylmethyl)pyridin-2-yl]amino}thiophene-3-carboxamide (435 mg, 0.95 mmol) in THF (15 mL) was added TBAF (1.0 M in THF, 2.38 mL, 2.38 mmol), and the reaction was stirred at room temperature for 6 h. The solution was diluted with water and extracted with EtOAc (2×). The organic extracts were dried over magnesium sulfate, filtered, combined with silica gel and evaporated. Flash chromatography (dry load, 0-10% MeOH/EtOAc) provided the title compound as a gray solid.

Workup

  1. extractionextracted with EtOAc (2×)
  2. dry with materialThe organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. dry with materialFlash chromatography (dry load, 0-10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-485d6586e8ec40e4a8dbe538bd9a1877
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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