Methylamine → N-Methylcarbamoylmethyl-Nicotinamide

HRID 533293Notes

Reaction equation

HRID 533293 reaction equation
CO[C:3](=[O:14])[CH2:4][NH:5][C:6]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:7].[CH3:15][NH2:16].[K+].[Br-]>C(O)C>[CH3:15][NH:16][C:3]([CH2:4][NH:5][C:6](=[O:7])[C:8]1[CH:13]=[CH:12][CH:11]=[N:10][CH:9]=1)=[O:14]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 253877Potassium BromideHCID 521804Glycine, N-(3-pyridinylcarbonyl)-, methyl ester

Product 1

HCID 59580557N-Methylcarbamoylmethyl-Nicotinamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

A suspension of [(pyridine-3-carbonyl)-amino]-acetic acid methyl ester (1.5 g, 7.7 mmol) and methylamine (33 wt % in absolute ethanol, 3.86 mL, 38.6 mmol) in ethanol (8 mL) was heated at 55° C. in a Parr reactor for 6 h. The mixture was cooled and then concentrated under reduced pressure to yield the product as a iridescent beige plates (1.41 g, 94%): 1H NMR (300 MHz, DMSO-d6) δ 9.05 (d, J=2.2 Hz, 1H), 9.00 (t, J=5.8 Hz, 1H), 8.77 (d, J=4.0 Hz, 1H), 8.23 (br d, J=8.1 Hz, 1H), 7.90 (q, J=4.1 Hz, 1H), 7.53 (dd, J=7.7, 4.7 Hz, 1H), 3.86 (d, J=5.8 Hz, 2H), 2.61 (d, J=4.4 Hz, 3H); IR (KBr) 3314, 1641 cm−1; ESIMS m/z 194 (M+1).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. customto yield the product as a iridescent beige plates (1.41 g, 94%)

Sources & evidence

ORD record
ord-504be8c5c6204e5ba79cb0f130e9769c
Source dataset
uspto-grants-2014_10
Patent number
US08853246B2

Reaction notes

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