Formic Acid → HCID 90203786, compound

HRID 1480284Notes

Reaction equation

HRID 1480284 reaction equation
[CH:1]1([C:4]2[C:5]([O:12][CH2:13][C:14]3([CH3:18])[CH2:17][O:16][CH2:15]3)=[CH:6][C:7](C#N)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[OH-].[K+].[CH:21]([OH:23])=[O:22]>C(O)C>[CH:1]1([C:4]2[C:5]([O:12][CH2:13][C:14]3([CH3:18])[CH2:15][O:16][CH2:17]3)=[CH:6][C:7]([C:21]([OH:23])=[O:22])=[N:8][CH:9]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 14797Potassium HydroxideHCID 90203924HCID 90203924, compound

Product 1

HCID 90203786HCID 90203786, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 5-cyclopropyl-4-((3-methyloxetan-3-yl)methoxy)picolinonitrile (1.73 g, 7.08 mmol) in ethanol (20 ml) in a microwave vial was added a 4.0M aqueous solution of potassium hydroxide (6.2 ml, 24.8 mmol). The vial was sealed and mixture was stirred at 85° C. overnight. The reaction was cooled down to 0° C. followed by addition of formic acid (1.14 g, 951 μl, 24.8 mmol) to acidify the reaction mixture. The crude solution was then evaporated to dryness and the crude material was directly purified by preparative HPLC to yield the title compound (1.34 g, 72%) as white solid. MS (ESI, m/z): 264.5 (M+H+).

Workup

  1. customThe vial was sealed
  2. temperatureThe reaction was cooled down to 0° C.
  3. customThe crude solution was then evaporated to dryness
  4. customthe crude material was directly purified by preparative HPLC

Sources & evidence

ORD record
ord-02075ad94ae6465fb2cc83fe110fc8f1
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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