Hydrochloric Acid → HCID 86705394, compound

HRID 926122Notes

Reaction equation

HRID 926122 reaction equation
C([O:3][C:4]([C:6]1[CH:15]=[N:14][C:13]2[N:12]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[C:11](=[O:25])[N:10]3[N:26]=[CH:27][N:28]=[C:9]3[C:8]=2[CH:7]=1)=[CH2:5])C.Cl.[OH-].[Na+]>O1CCOCC1>[C:4]([C:6]1[CH:15]=[N:14][C:13]2[N:12]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)[C:11](=[O:25])[N:10]3[N:26]=[CH:27][N:28]=[C:9]3[C:8]=2[CH:7]=1)(=[O:3])[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86705395HCID 86705395, compound

Product 1

HCID 86705394HCID 86705394, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

9-(1-Ethoxyvinyl)-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 32, 147 mg, 0.39 mmol) was suspended in dioxane (6 mL) and 6 N hydrochloric acid (3 mL) and stirred for 4 h. The mixture was basified to pH 11 with 1 N sodium hydroxide and extracted with DCM (3×15 mL). The combined extracts were dried (MgSO4) and concentrated to afford 122 mg (90%) of the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 2.73 (s, 3H), 3.76 (s, 3H), 5.79 (s, 2H), 6.78-6.89 (m, 2H), 7.56-7.66 (m, 2H), 8.39 (s, 1H), 9.13 (d, J=2.26 Hz, 1H), 9.35 (d, J=2.26 Hz, 1H). [M+H]=350.2.

Workup

  1. extractionextracted with DCM (3×15 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0c20d5e78aa74fdcaa06a43056e3a011
Source dataset
uspto-grants-2016_03
Patent number
US09284335B2

Reaction notes

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