Hydrochloric Acid → HCID 86690782, compound

HRID 1471743Notes

Reaction equation

HRID 1471743 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[C:11]([O:12][CH2:13][C:14]2[C:15]([C:20]3[N:21]([CH:25]([CH3:27])[CH3:26])[N:22]=[CH:23][N:24]=3)=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:10][N:9]=[C:8]([O:28][CH3:29])[CH:7]=1.Cl>>[CH:25]([N:21]1[C:20]([C:15]2[C:14]([CH2:13][O:12][C:11]3[C:6]([CH:2]=[O:1])=[CH:7][C:8]([O:28][CH3:29])=[N:9][CH:10]=3)=[CH:19][CH:18]=[CH:17][N:16]=2)=[N:24][CH:23]=[N:22]1)([CH3:27])[CH3:26]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86690780HCID 86690780, compound

Product 1

HCID 86690782HCID 86690782, compoundYield 99%

Conditions

Temperature
40 °C

Procedure

To 4-(1,3-dioxolan-2-yl)-5-((2-(2-isopropyl-2H-1,2,4-triazol-3-yl)pyridin-3-yl)methoxy)-2-methoxypyridine (60 mg, 0.15 mmol, 1 eq.) in a RB flask was added HCl (6 N, 2.0 mL). The mixture was warmed to 40° C., O/N, cooled to rt, neutralized to pH 7-8 with NaHCO3(sat) solution, and extracted with EtOAc three times. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give 5-((2-(2-isopropyl-2H-1,2,4-triazol-3-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde (52.2 mg, 99%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 10.35 (s, 1H), 8.62 (dd, J=4.6, 1.2 Hz, 1H), 8.33 (s, 1H), 8.11 (dd, J=8.0, 1.2 Hz, 1H), 7.98 (s, 1H), 7.40 (dd, J=8.0, 4.7 Hz, 1H), 6.99 (s, 1H), 5.62 (s, 2H), 5.28 (sep, J=6.7 Hz, 1H), 3.82 (s, 3H), 1.46 (d, J=6.7 Hz, 6H). LRMS (M+H+) m/z 354.1.

Workup

  1. temperatureO/N, cooled to rt
  2. extractionextracted with EtOAc three times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9899fc4cb2844cf1a0ce015ac92527be
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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