(S)-3-{4-[2-(4-Cyano-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester → (S)-3-{4-[2-(4-Cyano-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy]-phenyl}-hex-4-ynoic acid

HRID 2272842Notes

Reaction equation

HRID 2272842 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][C@@H:6]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]3[N:22]([N:24]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=4)[N:26]=3)[CH:23]=2)=[CH:12][CH:11]=1)[C:7]#[C:8][CH3:9])C>C1COCC1>[C:33]([C:30]1[CH:29]=[CH:28][C:27]([C:25]2[N:26]=[C:21]3[CH:20]=[CH:19][C:18]([CH2:17][O:16][C:13]4[CH:14]=[CH:15][C:10]([C@@H:6]([C:7]#[C:8][CH3:9])[CH2:5][C:4]([OH:35])=[O:3])=[CH:11][CH:12]=4)=[CH:23][N:22]3[N:24]=2)=[CH:32][CH:31]=1)#[N:34]

Participants

3

Reactant 1

HCID 118130002(S)-3-{4-[2-(4-Cyano-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester

Product 1

HCID 118129979(S)-3-{4-[2-(4-Cyano-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy]-phenyl}-hex-4-ynoic acidYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-3-{4-[2-(4-cyano-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester (0.130 g, 0.2795 mmol) in THF (10 mL) is added potassium trimethylsilanoate (0.143 g, 1.118 mmol) and the reaction mixture is stirred at room temperature for 2 hours. The reaction mixture is evaporated to dryness, the residue is washed with n-pentane, redissolved in water (5 mL) and is acidified with saturated citric acid solution (pH ˜5). The precipitated solid is filtered, washed with water, and dried to give the title compound as an off-white solid (0.113 g, 56.5%). LCMS m/z 437 (M+H)+.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. washthe residue is washed with n-pentane
  3. dissolutionredissolved in water (5 mL)
  4. filtrationThe precipitated solid is filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-c192afb91c5c425ba2be0835652e1721
Source dataset
uspto-grants-2015_09
Patent number
US09120793B2

Reaction notes

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