Methylamine → HCID 59580571, compound

HRID 533295Notes

Reaction equation

HRID 533295 reaction equation
CO[C:3](=[O:15])[CH2:4][NH:5][C:6]([C:8]1[CH:9]=[N:10][CH:11]=[C:12]([F:14])[CH:13]=1)=[O:7].[CH3:16][NH2:17]>C(O)C>[F:14][C:12]1[CH:11]=[N:10][CH:9]=[C:8]([CH:13]=1)[C:6]([NH:5][CH2:4][C:3](=[O:15])[NH:17][CH3:16])=[O:7]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59580613HCID 59580613, compound

Product 1

HCID 59580571HCID 59580571, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of [(5-fluoropyridine-3-carbonyl)-amino]-acetic acid methyl ester (2.96 g, 14.0 mmol) in ethanol (15 mL) was added methylamine (1.5 g, 33 wt % solution in ethanol, 70 mmol). This clear solution was then immediately put onto a 55° C. heating mantle for 10 min at which time the product had precipitated out of solution. The mixture was filtered in vacuo and the precipitate was washed with ethanol. The filtrate was concentrated and recrystallized from hot ethanol. This process was repeated again to give a white fluffy material (2.11 g, 72%): mp 201-202° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.10 (m, 1H), 8.93 (s, 1H), 8.76 (d, J=2.5 Hz, 1H), 8.10 (m, 1H), 7.95 (br s, 1H), 3.86 (d, J=5.8 Hz, 2H), 2.61 (d, J=4.4 Hz, 3H); ESIMS m/z 212 (M+1), m/z 210 (M−1).

Workup

  1. customwas then immediately put onto a 55° C.
  2. temperatureheating mantle for 10 min at which time the product
  3. customhad precipitated out of solution
  4. filtrationThe mixture was filtered in vacuo
  5. washthe precipitate was washed with ethanol
  6. concentrationThe filtrate was concentrated
  7. customrecrystallized from hot ethanol

Sources & evidence

ORD record
ord-d3c7817ead384342ac68a9f80832e280
Source dataset
uspto-grants-2014_10
Patent number
US08853246B2

Reaction notes

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