N-Methyl-D-glucamine → HCID 15860287, compound

HRID 2184771Notes

Reaction equation

HRID 2184771 reaction equation
CO[C:3]([C:5]1[CH:10]=[N:9][C:8]([C:11]([O:13]C)=O)=[CH:7][N:6]=1)=[O:4].[CH3:15][NH:16][CH2:17][C@@H:18]([C@H:20]([C@@H:22]([C@@H:24]([CH2:26]O)[OH:25])[OH:23])[OH:21])[OH:19]>C(O)C>[CH3:15][N:16]([CH2:17][C@H:18]([OH:19])[C@@H:20]([OH:21])[C@H:22]([OH:23])[C@H:24]([OH:25])[CH3:26])[C:11]([C:8]1[CH:7]=[N:6][C:5]([C:3]([N:16]([CH3:15])[CH2:17][C@H:18]([OH:19])[C@@H:20]([OH:21])[C@H:22]([OH:23])[C@H:24]([OH:25])[CH3:26])=[O:4])=[CH:10][N:9]=1)=[O:13]

Participants

4

Reactant 2

HCID 8567N-Methyl-D-glucamineHCID 518685Dimethyl pyrazine-2,5-dicarboxylate

Product 1

HCID 15860287HCID 15860287, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 392 mg of 2,5-dimethoxycarbonylpyrazine and 780 mg of N-methylglucamine in 5 cm3 of ethanol is heated at a temperature close to the reflux temperature for 3 hours and the reaction mixture is filtered while hot. The white solid is washed with twice 10 cm3 of boiling ethanol. 1000 mg of N-methyl-N-[(2S,3R,4R,5R)-2,3,4,5-tetrahydroxy-1-hexyl]-N′-methyl-N′-[(2S,3R,4R,5R)-2,3,4,5-tetrahydroxy-1-hexyl]-pyrazine-2,5-dicarboxamide are thus obtained in the form of a white solid melting at 152° C. [1H NMR spectrum (400 MHz, (CD3)2SO-d6, at a temperature of 403 K, δ in ppm): 3.14 (s, 6H: 2×NCH3); from 3.45 to 4.28 (mts, 16H: 8×CHO−2×CH2 and 2×CH2N); 8.78 (s, 2H: ═CH at 3 and ═CH at 6)].

Workup

  1. customclose to the reflux temperature for 3 hours
  2. filtrationthe reaction mixture is filtered while hot
  3. washThe white solid is washed with twice 10 cm3 of boiling ethanol

Sources & evidence

ORD record
ord-c2716bca4b044fa9a872ddef8b6adbd1
Source dataset
uspto-grants-2002_06
Patent number
US06399613B1

Reaction notes

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