Hydrochloric Acid → HCID 86705392, compound

HRID 926121Notes

Reaction equation

HRID 926121 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[N:9]([N:24]=[CH:25][N:26]=3)[C:10](=[O:23])[N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:12]=2[N:13]=1.C1COCC1.Cl.C(=O)(O)[O-].[Na+]>O>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][N:11]2[C:12]3[N:13]=[C:4]([CH:3]=[O:2])[CH:5]=[CH:6][C:7]=3[C:8]3=[N:26][CH:25]=[N:24][N:9]3[C:10]2=[O:23])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 86705393HCID 86705393, compound

Product 1

HCID 86705392HCID 86705392, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

8-(Dimethoxymethyl)-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 3, 682 mg, 1.79 mmol), THF (20 mL), water (5 mL) and 12 N hydrochloric acid (3 mL) were combined and stirred at room temperature for 20 h. The mixture was neutralized slowly with powdered sodium bicarbonate to pH 8. The mixture was diluted with water (20 mL) and extracted with EtOAc (3×20 mL). The combined extracts were dried (MgSO4) and concentrated to afford the title compound (516 mg, 77%) as a yellow foam, which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 3.73-3.81 (m, 3H), 5.83, (s, 2H), 6.85 (d, J=8.66 Hz, 2H), 7.64 (d, J=8.53 Hz, 2H), 8.03 (d, J=7.78 Hz, 1H), 8.42 (s, 1H), 8.83 (d, J=7.91 Hz, 1H), 10.22 (s, 1H). [M+H]=336.1.

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e2ee8735c54e427c9049fe7783b38e49
Source dataset
uspto-grants-2016_03
Patent number
US09284335B2

Reaction notes

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