Hydrochloric Acid → HCID 85473370, compound

HRID 1471746Notes

Reaction equation

HRID 1471746 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:24]([CH:25]([CH3:27])[CH3:26])[N:23]=[CH:22][C:21]=3[CH3:28])=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:10][N:9]=[C:8]([O:29][CH3:30])[CH:7]=1.Cl>>[CH:25]([N:24]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:29][CH3:30])=[N:9][CH:10]=3)=[CH:19][CH:18]=[CH:17][N:16]=2)=[C:21]([CH3:28])[CH:22]=[N:23]1)([CH3:27])[CH3:26]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86690783HCID 86690783, compound

Product 1

HCID 85473370HCID 85473370, compoundYield 99%

Conditions

Temperature
40 °C

Procedure

To 4-(1,3-dioxolan-2-yl)-5-((2-(1-isopropyl-4-methyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxypyridine (41 mg, 0.1 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, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 5-((2-(1-isopropyl-4-methyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde (33.3 mg, 99%) as an pale-yellow oil. 1H NMR (400 MHz, CDCl3) δ 10.32 (s, 1H), 8.71 (dd, J=4.7, 1.6 Hz, 1H), 7.99 (dd, J=7.9, 1.5 Hz, 1H), 7.76 (s, 1H), 7.40 (dd, J=7.1, 4.7 Hz, 1H), 7.39 (s, 1H), 7.01 (s, 1H), 4.86-4.99 (m, 2H), 4.12 (sep, J=6.7, 1H), 3.82 (s, 3H), 1.86 (s, 3H), 1.40 (d, J=767 Hz, 3H), 1.29 (d, J=6.7 Hz, 3H). LRMS (M+H+) m/z 367.1.

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
  6. custompurified on silica gel using
  7. additiona mixture of EtOAc and hexanes as eluent

Sources & evidence

ORD record
ord-01892248c8a144b0a70c47e2f6656b51
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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