N-{3-[2-amino-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-cyano-4-pyridinyl]phenyl}-5-oxotetrahydro-2-furancarboxamide → HCID 135469510, compound

HRID 2218249Notes

Reaction equation

HRID 2218249 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[C:12]([NH:16][C:17]([CH:19]3[CH2:23][CH2:22][C:21](=[O:24])[O:20]3)=[O:18])[CH:13]=[CH:14][CH:15]=2)[CH:5]=[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][Si](C(C)(C)C)(C)C)[N:3]=1>C1COCC1>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[C:12]([NH:16][C:17]([CH:19]3[CH2:23][CH2:22][C:21](=[O:24])[O:20]3)=[O:18])[CH:13]=[CH:14][CH:15]=2)[CH:5]=[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[OH:31])[N:3]=1

Participants

3

Reactant 1

HCID 69145261N-{3-[2-amino-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-cyano-4-pyridinyl]phenyl}-5-oxotetrahydro-2-furancarboxamide

Product 1

HCID 135469510HCID 135469510, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold (0° C.) solution of N-{3-[2-amino-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-cyano-4-pyridinyl]phenyl}-5-oxotetrahydro-2-furancarboxamide (0.400 g, 0.757 mmol) in THF (5 mL) was added dropwise a solution n-tetrabutylammonium fluoride in THF (1M, 2 mL). After being stirred for 30 minutes, the mixture was quenched with water (5 mL). The resulting precipitate was collected by filtration, washed with water and ethanol, and dried under reduced pressure to give N-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-5-oxotetrahydro-2-furancarboxamide as a white solid (0.293 g, yield 93%).

Workup

  1. customthe mixture was quenched with water (5 mL)
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water and ethanol
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-436d103b22774424b761c0350ba15be9
Source dataset
uspto-grants-2008_08
Patent number
US07410986B2

Reaction notes

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