Hydrochloric Acid → HCID 86705392, compound

HRID 707480Notes

Reaction equation

HRID 707480 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.O1CCCC1.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 (682 mg, 1.79 mmol), tetrahydrofuran (20 ml), water (5 ml) and 12 N hydrochloric acid (3 ml) were combined and stirred at room temperature for 20 hours. The mixture was neutralized slowly with powdered sodium bicarbonate to pH 8. The mixture was diluted with water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined extracts were dried (MgSO4) and concentrated to afford 516 mg (77%) of the aldehyde 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). LCMS (MH+, 336.1).

Workup

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

Sources & evidence

ORD record
ord-cd4046c8c58e46da88d2f589d5d1498b
Source dataset
uspto-grants-2015_11
Patent number
US09175010B2

Reaction notes

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