3-Amino-1,2-propanediol → HCID 15860289, compound

HRID 2184773Notes

Reaction equation

HRID 2184773 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].[NH2:15][CH2:16][CH:17]([OH:20])[CH2:18][OH:19]>C(O)C>[OH:20][CH:17]([CH2:18][OH:19])[CH2:16][NH:15][C:11]([C:8]1[CH:7]=[N:6][C:5]([C:3]([NH:15][CH2:16][CH:17]([OH:20])[CH2:18][OH:19])=[O:4])=[CH:10][N:9]=1)=[O:13]

Participants

4

Reactant 2

HCID 735613-Amino-1,2-propanediolHCID 518685Dimethyl pyrazine-2,5-dicarboxylate

Product 1

HCID 15860289HCID 15860289, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 490 mg of 2,5-dimethoxycarbonylpyrazine and 0.40 cm3 of 3-amino-1,2-propanediol in 5 cm3 of ethanol is heated at a temperature in the region of the reflux temperature for 3 hours. The reaction mixture is filtered while hot. The white solid is washed with 3 times 15 cm3 of boiling ethanol. 416 mg of N,N′-bis(2,3-dihydroxy-1-propyl)pyrazine-2,5-dicarboxamide are thus obtained in the form of a white solid melting at 234° C. [1H NMR spectrum (400 MHz, (CD3)2SO-d6, δ in ppm): from 3.20 to 3.60 (mt, 8H: 2×OCH2 and 2×NCH2); 3.68 (mt, 2H: 2×OCH); 4.67 (t, J=5.5 Hz, 2H: OH at 2γ and OH at 5γ); 4.95 (d, J=5 Hz, 2H: OH at 2β and OH at 5β); 8.79 (t, J=5.5 Hz, 2H: 2×CONH); 9.23 (s, 2H: ═CH at 3 and ═CH at 6)].

Workup

  1. filtrationThe reaction mixture is filtered while hot
  2. washThe white solid is washed with 3 times 15 cm3 of boiling ethanol

Sources & evidence

ORD record
ord-dc06b648f69448f08610f30a455ae60d
Source dataset
uspto-grants-2002_06
Patent number
US06399613B1

Reaction notes

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