Methylamine → HCID 47315722, compound

HRID 2199188Notes

Reaction equation

HRID 2199188 reaction equation
CO[C:3](=[O:15])[CH:4]([NH:6][C:7]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:8])[CH3:5].[CH3:16][NH2:17]>C(O)C>[CH3:16][NH:17][C:3]([CH:4]([NH:6][C:7](=[O:8])[C:9]1[CH:14]=[CH:13][CH:12]=[N:11][CH:10]=1)[CH3:5])=[O:15]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 19166803HCID 19166803, compound

Product 1

HCID 47315722HCID 47315722, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 2-[(pyridine-3-carbonyl)-amino]-propionic acid methyl ester (10.4 g, 50 mmol) in ethanol (50 mL) was added methylamine (24 g, 33 wt % solution in ethanol, 250 mmol). The reaction mixture was heated at 55° C. for 45 min. The solvents were removed in vacuo and the residue was recrystallized from hot ethyl acetate and hexanes. The yellow crystals thus obtained were washed with cold ethyl acetate and dried to give the desired product (5.2 g, 50%): 1H NMR (300 MHz, DMSO-d6) δ 9.05 (br s, 1H), 8.77-8.70 (m, 2H), 8.24 (m, 2H), 7.89 (br s, 1H), 7.50 (m, 1H), 2.59 (d, J=4.7 Hz, 3H), 1.33 (d, J=7.4 Hz, 3H); ESIMS m/z 208.1 (M+1), m/z 206.1 (M−1).

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was recrystallized from hot ethyl acetate and hexanes
  3. customThe yellow crystals thus obtained
  4. washwere washed with cold ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-00f991d7fe1e4614b5ba35141f2bd29c
Source dataset
uspto-grants-2016_06
Patent number
US09357780B2

Reaction notes

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