HCID 68540457, compound → HCID 68543984, compound

HRID 2242907Notes

Reaction equation

HRID 2242907 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[N:7]([N:24]=[C:25]([C:27]3[O:28][CH:29]=[CH:30][CH:31]=3)[N:26]=2)[CH:8]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[N:10]=1)=[O:4]>CO.[OH-].[K+]>[C:20]([O:19][C:17]([N:14]1[CH2:13][CH2:12][N:11]([C:9]2[N:10]=[C:5]([C:3]([OH:4])=[O:2])[C:6]3[N:7]([N:24]=[C:25]([C:27]4[O:28][CH:29]=[CH:30][CH:31]=4)[N:26]=3)[CH:8]=2)[CH2:16][CH2:15]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

3

Reactant 1

HCID 68540457HCID 68540457, compound

Product 1

HCID 68543984HCID 68543984, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 23689386Potassium hydroxide methanolSolvent

Procedure

A solution of 6-(4-tert-butoxycarbonyl-piperazin-1-yl)-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazine-8-carboxylic acid methyl ester (4 mg, 0.009 mmol; see Example 16 (g) above) in 1 N potassium hydroxide methanol solution (1 mL) was stirred at room temperature for 2 hours. The solvent was then removed, and the residue was suspended in water. The resulting suspension was acidified with acetic acid until pH 4 and extracted with methylene chloride three times. The combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, and concentrated to afford 6-(4-tert-butoxycarbonyl-piperazin-1-yl)-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazine-8-carboxylic acid as a yellow solid (2.6 mg, 68%). 1H NMR (300 MHz, CDCl3) δ1.50 (s, 9H), 3.53-3.58 (m, 4H), 3.63-3.68 (m, 4H), 6.63 (dd, J=1.8, 3.3 Hz, 1H), 7.35 (d, J=3.3 Hz, 1H), 7.67 (d, J=1.8 Hz, 1H), 8.08 (s, 1 H); 13C NMR (100 MHz, CDCl3) δ28.39, 45.90, 80.49, 106.62, 112.27, 113.83, 134.92, 142.08, 144.56, 145.30, 149.18, 154.60, 157.09, 161.49.

Workup

  1. customwas stirred at room temperature for 2 hours
  2. customThe solvent was then removed
  3. extractionextracted with methylene chloride three times
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8d7a0bc6263a4a639eba403956a923da
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

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