2-Amino-2-methyl-1,3-propanediol → HCID 22458023, compound

HRID 2184778Notes

Reaction equation

HRID 2184778 reaction equation
CO[C:3]([C:5]1[CH:10]=[N:9][CH:8]=[C:7]([C:11]([O:13]C)=O)[N:6]=1)=[O:4].[NH2:15][C:16]([CH3:21])([CH2:19][OH:20])[CH2:17][OH:18]>C(O)C>[OH:18][CH2:17][C:16]([NH:15][C:11]([C:7]1[CH:8]=[N:9][CH:10]=[C:5]([C:3]([NH:15][C:16]([CH3:21])([CH2:19][OH:20])[CH2:17][OH:18])=[O:4])[N:6]=1)=[O:13])([CH3:21])[CH2:19][OH:20]

Participants

4

Reactant 2

HCID 15312-Amino-2-methyl-1,3-propanediolHCID 14715227Dimethyl pyrazine-2,6-dicarboxylate

Product 1

HCID 22458023HCID 22458023, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 500 mg of 2,6-dimethoxycarbonylpyrazine and 525 mg of 2-amino-2-methyl-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 cooled to a temperature of 20° C. and the white solid formed is then filtered off and washed with twice 5 cm3 of ethanol. 260 mg of N,N′-bis(1,3-dihydroxy-2-methyl-2-propyl)pyrazine-2,6-dicarboxamide are thus obtained in the form of a white solid melting at 169° C. [1H NMR spectrum (400 MHz, (CD3)2SO-d6, δ in ppm): 1.34 (s, 6H: 2×CH3); 3.61 and 3.69 (2 dd, J=11 and 5.5 Hz, 8H: 4×CH2O); 4.88 (t, J=5.5 Hz, 4H: 4×OH); 8.16 (s, 2H: 2×CONH); 9.35 (s, 2H: ═CH at 3 and ═CH at 5)].

Workup

  1. customthe white solid formed
  2. filtrationis then filtered off
  3. washwashed with twice 5 cm3 of ethanol

Sources & evidence

ORD record
ord-4a64d9e37395470a8c5a431e8f04e6d8
Source dataset
uspto-grants-2002_06
Patent number
US06399613B1

Reaction notes

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