Methylamine → HCID 59580571, compound

HRID 1470402Notes

Reaction equation

HRID 1470402 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-508cae605bf84c298552c61bce337672
Source dataset
uspto-grants-2015_04
Patent number
US09006446B2

Reaction notes

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