Hydrochloric Acid → HCID 85473238, compound

HRID 1471723Notes

Reaction equation

HRID 1471723 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[N:9]=[CH:8][C:7]=1[O:14][CH2:15][C:16]1[C:17]([C:22]([OH:25])([CH3:24])[CH3:23])=[N:18][CH:19]=[CH:20][CH:21]=1.Cl>>[OH:25][C:22]([C:17]1[C:16]([CH2:15][O:14][C:7]2[C:6]([CH:2]=[O:1])=[CH:11][C:10]([O:12][CH3:13])=[N:9][CH:8]=2)=[CH:21][CH:20]=[CH:19][N:18]=1)([CH3:23])[CH3:24]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86690765HCID 86690765, compound

Product 1

HCID 85473238HCID 85473238, compoundYield 99%

Conditions

Temperature
40 °C

Procedure

To 2-(3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)pyridin-2-yl)propan-2-ol (30 mg, 0.087 mmol, 1 eq.) in a RB flask was added HCl (6 N, 3.0 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 twice. 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-(2-hydroxypropan-2-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde (10.2 mg, 99%) as a pale-yellow oil. 1H NMR (400 MHz, CDCl3) δ 10.36 (s, 1H), 8.46 (dd, J=4.7, 1.6 Hz, 1H), 7.99 (s, 1H), 7.86 (dd, J=7.8, 1.5 Hz, 1H), 7.24 (dd, J=7.8, 4.7 Hz, 1H), 7.05 (s, 1H), 5.37 (s, 2H), 3.85 (s, 3H), 1.57 (s, 6H). LRMS (M+H+) m/z 303.1.

Workup

  1. temperatureO/N, cooled to rt
  2. extractionextracted with EtOAc twice
  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-55377c0f23d94cc4967264d256309c97
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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