Serinol → HCID 15860288, compound

HRID 2184772Notes

Reaction equation

HRID 2184772 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][CH:16]([CH2:19][OH:20])[CH2:17][OH:18]>C(O)C>[OH:18][CH2:17][CH:16]([NH:15][C:11]([C:8]1[CH:7]=[N:6][C:5]([C:3]([NH:15][CH:16]([CH2:19][OH:20])[CH2:17][OH:18])=[O:4])=[CH:10][N:9]=1)=[O:13])[CH2:19][OH:20]

Participants

4

Reactant 2

HCID 68294SerinolHCID 518685Dimethyl pyrazine-2,5-dicarboxylate

Product 1

HCID 15860288HCID 15860288, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 392 mg of 2,5-dimethoxycarbonylpyrazine and 364 mg of 2-amino-1,3-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 10 cm3 of boiling ethanol. 530 mg of N,N′-bis(1,3-dihydroxy-2-propyl)pyrazine-2,5-dicarboxamide are thus obtained in the form of a white solid melting at 218° C. [1H NMR spectrum (400 MHz, (CD3)2SO-d6, δ in ppm): from 3.45 to 3.65 (mt, 8H: 4×CH2O); 4.02 (mt, 2H: 2×NCH); 4.85 (t, J=5.5 Hz, 4H: 4×OH); 8.48 (d, J=9 Hz, 2H: 2×CONH); 9.25 (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 10 cm3 of boiling ethanol

Sources & evidence

ORD record
ord-87df94c8402c4d7a8c47b75630cabb9d
Source dataset
uspto-grants-2002_06
Patent number
US06399613B1

Reaction notes

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