Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86609049, compound

HRID 1619207Notes

Reaction equation

HRID 1619207 reaction equation
CO[C:3]([C:5]1[CH2:6][CH2:7][N:8]([C:11]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH2:9][CH:10]=1)=[O:4].Cl.[CH3:18][NH:19][O:20][CH3:21].C([Mg]Cl)(C)C>C1COCC1>[CH3:21][O:20][N:19]([CH3:18])[C:3]([C:5]1[CH2:6][CH2:7][N:8]([C:11]2[N:12]=[CH:13][CH:14]=[CH:15][N:16]=2)[CH2:9][CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 57420153HCID 57420153, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 86609049HCID 86609049, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

To a suspension of 1-pyrimidin-2-yl-1,2,3,6-tetrahydro-pyridin-4-carboxylic acid methyl ester (73.8 mg, 0.337 mmol) and N-methyl-O-methyl hydroxylamine hydrochloride (51.0 mg, 0.552 mmol) in THF (3 ml), was added isopropyl magnesium chloride (2.0 M in THF, 0.505 ml) at −20° C. over 15 minute-period. The mixture was stirred at −10° C. for another 30 minutes before it was quenched with the addition of saturated ammonium chloride (10 ml). The mixture was extracted with EtOAc (2×15 ml). The combined organic layers were washed with brine (15 ml), dried (MgSO4), filtered, and concentrated under reduced pressure to furnish the crude product. This material was purified by column chromatography (4% MeOH/CH2Cl2) to give 1-pyrimidin-2-yl-1,2,3,6-tetrahydro-pyridin-4-carboxylic acid methoxy-methyl amide (48 mg, 58%) as white crystals: 1H NMR (CDCl3, 400 MHz) δ 8.35 (d, J=6.4 Hz, 2H), 6.53 (t, J=6.4 Hz, 1H), 6.43 (m, 1H), 4.35 (m, 2H), 3.99 (t, J=5.6 Hz, 2H), 3.66 (s, 3H), 3.27 (s, 3H), 2.55 (m, 2H).

Workup

  1. customwas quenched with the addition of saturated ammonium chloride (10 ml)
  2. extractionThe mixture was extracted with EtOAc (2×15 ml)
  3. washThe combined organic layers were washed with brine (15 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto furnish the crude product
  8. customThis material was purified by column chromatography (4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-6d40cc91544d4b76a066f1d67b80172f
Source dataset
uspto-grants-2014_07
Patent number
US08772291B2

Reaction notes

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