Hydrochloric Acid → HCID 86705389, compound

HRID 926116Notes

Reaction equation

HRID 926116 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]2[C:13]3[N:14]=[CH:15][C:16]([CH2:18][O:19]COC)=[CH:17][C:12]=3[C:11]3=[N:23][CH:24]=[N:25][N:10]3[C:9]2=[O:26])=[CH:5][CH:4]=1.Cl>CO>[OH:19][CH2:18][C:16]1[CH:15]=[N:14][C:13]2[N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:28][CH:27]=3)[C:9](=[O:26])[N:10]3[N:25]=[CH:24][N:23]=[C:11]3[C:12]=2[CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86705390HCID 86705390, compound

Product 1

HCID 86705389HCID 86705389, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 6-(4-methoxybenzyl)-9-((methoxymethoxy)methyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 31, 40 mg, 0.10 mmol), methanol (0.80 mL) and 5 N hydrochloric acid (0.40 mL) was stirred at 50° C. for 16 h. The mixture was extracted with DCM (1 mL), basified to pH 14 with 15% aqueous sodium hydroxide and extracted with DCM (2 mL). The combined DCM extracts were concentrated under reduced pressure. Purification (HPLC, 10-90% ACN-water) afforded the title compound (21 mg, 59%) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ 3.69 (s, 3H), 4.69 (d, J=4.6 Hz, 2H), 5.54 (t, J=4.6 Hz, 1H), 5.59 (s, 2H), 6.84 (d, J=6.9 Hz, 2H), 7.36 (d, J=6.9 Hz, 2H), 8.58 (d, J=1.6 Hz, 1H), 8.60 (s, 1H), 8.72 (d, J=1.6 Hz, 1H). [M+H]=338.1.

Workup

  1. extractionThe mixture was extracted with DCM (1 mL)
  2. extractionextracted with DCM (2 mL)
  3. concentrationThe combined DCM extracts were concentrated under reduced pressure
  4. customPurification (HPLC, 10-90% ACN-water)

Sources & evidence

ORD record
ord-ce58e063feac415c8e99db5d66ad042f
Source dataset
uspto-grants-2016_03
Patent number
US09284335B2

Reaction notes

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