Hydrochloric Acid → HCID 70873624, compound

HRID 2208824Notes

Reaction equation

HRID 2208824 reaction equation
[CH2:1]([N:3]([CH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[C:4]1[C:5]([CH3:14])=[C:6]([C:10]([O:12]C)=[O:11])[CH:7]=[N:8][CH:9]=1)[CH3:2].[OH-].[Na+].Cl>C1COCC1.CO>[CH2:1]([N:3]([CH:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1)[C:4]1[C:5]([CH3:14])=[C:6]([C:10]([OH:12])=[O:11])[CH:7]=[N:8][CH:9]=1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70873937HCID 70873937, compound

Product 1

HCID 70873624HCID 70873624, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 5-[ethyl(oxan-4-yl)amino]-4-methylpyridine-3-carboxylate (415 mg, 1.49 mmol) in THF (7 ml) and MeOH (3 ml) was added 4M NaOH solution (932 μl, 3.73 mmol). The reaction was stirred at room temperature for 4.5 h after which the solution was neutralised via the addition of 1M HCl and the solvent was removed under reduced pressure, followed by the addition of saturated brine (10 ml). The aqueous phase was extracted with 1:1 IPA:CHCl3 (3×50 ml), the combined organics washed with brine (30 ml), dried using Na2SO4, filtered and evaporated to afford the title compound as an off-white solid (305 mg, 77%) which was suitable for use in the next stage without any further purification. LC-MS 99%, m/z=265.1, 1H NMR (500 MHz, DMSO-d6) δ 8.57 (s, 1H), 8.46 (s, 1H), 3.82 (d, J=11.6 Hz, 2H), 3.25 (t, J=10.9 Hz, 2H), 3.16-2.99 (m, 3H), 2.45 (s, 3H), 1.64 (d, J=11.0 Hz, 2H), 1.48 (dt, J=11.9, 5.7 Hz, 2H), 0.81 (t, J=7.0 Hz, 3H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionfollowed by the addition of saturated brine (10 ml)
  3. extractionThe aqueous phase was extracted with 1:1 IPA
  4. washCHCl3 (3×50 ml), the combined organics washed with brine (30 ml)
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-9f75d7bedb124d2e90c134173101fc46
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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